Synthesis of indoles from N-(trifluoroacetyl)-2-anilino acetals

JE Nordlander, DB Catalane, KD Kotian…

Index: Nordlander, J. Eric; Catalane, David B.; Kotian, Kirtivan D.; Stevens, Randall M.; Haky, Jerome E. Journal of Organic Chemistry, 1981 , vol. 46, p. 778 - 782

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Citation Number: 49

Abstract

N-(Trifluoroacety1) indole (3 (X= H)) was isolated by distillation and identified by matching its' H NMR spectrum with that recently reported by Clementi, Linda, and co-workers for the same compound obtained from direct trifluoroacetylation of ind01e. l~ The 4, 6-dimethyl analogue, 3 (X= 4, 6-Mez), was purified by recrystallization and characterized by NMR and elemental analysis. The remaining intermediates 3 were not isolated, but NMR spectra of ...

 Related Synthetic Route
p-Toluidine Structure

106-49-0

p-Toluidine

Bromoacetaldehyde diethyl acetal Structure

2032-35-1

Bromoacetaldehy...

~66%

N1-(2,2-DIETHOXYETHYL)-4-METHYLANILINE Structure

75934-28-0

N1-(2,2-DIETHOX...

Learn More
N-(2,2-diethoxyethyl)-3-methoxyaniline Structure

32431-44-0

N-(2,2-diethoxy...

~%

4-Methoxyindole Structure

4837-90-5

4-Methoxyindole

Learn More
3-anisidine Structure

536-90-3

3-anisidine

~%

4-Methoxyindole Structure

4837-90-5

4-Methoxyindole

Learn More
Structure

75934-38-2

~%

6-Methoxyindole Structure

3189-13-7

6-Methoxyindole

4-Methoxyindole Structure

4837-90-5

4-Methoxyindole

Learn More
Structure

74497-02-2

Bromoacetaldehyde diethyl acetal Structure

2032-35-1

Bromoacetaldehy...

~76%

N-(2,2-diethoxyethyl)aniline Structure

22758-34-5

N-(2,2-diethoxy...

Learn More
N-(2,2-diethoxyethyl)-N-(3,5-dimethylphenyl)-2,2,2-trifluoroacetamide Structure

75934-34-8

N-(2,2-diethoxy...

~0%

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

4,6-dimethyl-1-trifluoroacetylindole Structure

75934-42-8

4,6-dimethyl-1-...

Learn More
N-(2,2-diethoxyethyl)-2,2,2-trifluoro-N-phenylacetamide Structure

75934-33-7

N-(2,2-diethoxy...

~0%

2,2,2-trifluoro-1-indol-1-ylethanone Structure

62615-78-5

2,2,2-trifluoro...

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

Learn More
N-(2,2-diethoxyethyl)-2,2,2-trifluoro-N-(p-tolyl)acetamide Structure

75934-36-0

N-(2,2-diethoxy...

~%

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

2,2,2-trifluoro-1-(5-methyl-1H-indol-1-yl)ethanone Structure

582319-44-6

2,2,2-trifluoro...

Learn More
N-(2,2-diethoxyethyl)-2,2,2-trifluoro-N-phenylacetamide Structure

75934-33-7

N-(2,2-diethoxy...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~%

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

N/A Structure

75948-78-6

N/A

Learn More
N-(2,2-diethoxyethyl)-N-(3,5-dimethylphenyl)-2,2,2-trifluoroacetamide Structure

75934-34-8

N-(2,2-diethoxy...

~93%

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

4,6-dimethyl-1-trifluoroacetylindole Structure

75934-42-8

4,6-dimethyl-1-...

Learn More
N/A Structure

75934-26-8

N/A

~%

4,6-dimethyl-1-trifluoroacetylindole Structure

75934-42-8

4,6-dimethyl-1-...

Learn More
3,5-Dimethylaniline Structure

108-69-0

3,5-Dimethylaniline

~%

4,6-dimethyl-1-trifluoroacetylindole Structure

75934-42-8

4,6-dimethyl-1-...

Learn More
3,4-Dimethylaniline Structure

95-64-7

3,4-Dimethylaniline

~%

5,6-Dimethyl-1H-indole Structure

30877-30-6

5,6-Dimethyl-1H...

Learn More
N-(2,2-diethoxyethyl)-3,4-dimethylaniline Structure

75934-27-9

N-(2,2-diethoxy...

~%

5,6-Dimethyl-1H-indole Structure

30877-30-6

5,6-Dimethyl-1H...

Learn More
N-(2,2-diethoxyethyl)-N-(3,4-dimethylphenyl)-2,2,2-trifluoroacetamide Structure

75934-35-9

N-(2,2-diethoxy...

~%

5,6-Dimethyl-1H-indole Structure

30877-30-6

5,6-Dimethyl-1H...

4,5-dimethyl-1H-indole Structure

27866-47-3

4,5-dimethyl-1H...

Learn More
N-(2,2-diethoxyethyl)-3,4-dimethylaniline Structure

75934-27-9

N-(2,2-diethoxy...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~%

5,6-Dimethyl-1H-indole Structure

30877-30-6

5,6-Dimethyl-1H...

4,5-dimethyl-1H-indole Structure

27866-47-3

4,5-dimethyl-1H...

Learn More
1-(4,7-dimethyl-1H-indol-1-yl)-2,2,2-trifluoroethanone Structure

582319-48-0

1-(4,7-dimethyl...

~%

4,7-Dimethyl-1H-indole Structure

5621-17-0

4,7-Dimethyl-1H...

Learn More
2-Amino-p-xylene Structure

95-78-3

2-Amino-p-xylene

~%

4,7-Dimethyl-1H-indole Structure

5621-17-0

4,7-Dimethyl-1H...

Learn More
N-(2,5-dimethylphenyl)aminoacetoaldehyde diethyl acetal Structure

75934-30-4

N-(2,5-dimethyl...

~%

4,7-Dimethyl-1H-indole Structure

5621-17-0

4,7-Dimethyl-1H...

Learn More
N-(2,2-diethoxyethyl)-N-(2,5-dimethylphenyl)-2,2,2-trifluoroacetamide Structure

75934-39-3

N-(2,2-diethoxy...

~%

4,7-Dimethyl-1H-indole Structure

5621-17-0

4,7-Dimethyl-1H...

Learn More
N-(2,2-diethoxyethyl)-2,2,2-trifluoro-N-phenylacetamide Structure

75934-33-7

N-(2,2-diethoxy...

~93%

2,2,2-trifluoro-1-indol-1-ylethanone Structure

62615-78-5

2,2,2-trifluoro...

Ethyl trifluoroacetate Structure

383-63-1

Ethyl trifluoro...

Learn More
N-(2,2-diethoxyethyl)aniline Structure

22758-34-5

N-(2,2-diethoxy...

Trifluoroacetic anhydride Structure

407-25-0

Trifluoroacetic...

~92%

2,2,2-trifluoro-1-indol-1-ylethanone Structure

62615-78-5

2,2,2-trifluoro...

Learn More
Structure

74497-02-2

~%

2,2,2-trifluoro-1-indol-1-ylethanone Structure

62615-78-5

2,2,2-trifluoro...

Learn More
N-(2,2-diethoxyethyl)aniline Structure

22758-34-5

N-(2,2-diethoxy...

~%

2,2,2-trifluoro-1-indol-1-ylethanone Structure

62615-78-5

2,2,2-trifluoro...

Learn More
4,6-dimethyl-1-trifluoroacetylindole Structure

75934-42-8

4,6-dimethyl-1-...

~98%

4,6-Dimethylindole Structure

75948-77-5

4,6-Dimethylindole

Learn More
3-anisidine Structure

536-90-3

3-anisidine

Bromoacetaldehyde diethyl acetal Structure

2032-35-1

Bromoacetaldehy...

~63%

N-(2,2-diethoxyethyl)-3-methoxyaniline Structure

32431-44-0

N-(2,2-diethoxy...

Learn More

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