The Journal of Organic Chemistry

Preparation of 2-hydroxyamino-. alpha.,. alpha.,. alpha.-trifluoro-p-toluenesulfonamide by catalytic hydrogenation and its use in the synthesis of 2, 3-dihydro-4H-1, 2, 4 …

HL Yale

Index: Yale,H.L. Journal of Organic Chemistry, 1968 , vol. 33, # 6 p. 2382 - 2385

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Citation Number: 2

Abstract

The hydrogenation of 2-nitro-~~,~~,~~-trifluoro-p-toluenesulfonamide (1) over a palladium catalyst in ethanol proceeded rapidly (0.5 hr) at room temperature; hydrogen uptake ceased with the absorption of 2 molar equiv to give a 90% yield of pure 2-hydroxyamino-cy, cu1~- trifluoro-p-to1uenesu1fonamide(2). Reduction of 2 to the amine (3) required a temperature of 50-60'and about 3 hr. The acid-catalyzed cyclization of 2 with formaldehyde and ...