Sodium Dithionite → 2-Methyl-4-nitroaniline

HRID 1612615Notes

Reaction equation

HRID 1612615 reaction equation
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21])=O)C1C=CC=CC=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>>[CH3:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[NH2:11]

Participants

3

Reactant 2

HCID 24489Sodium DithioniteHCID 305261benzyl N-(2-methyl-4-nitrophenyl)carbamate

Product 1

HCID 74412-Methyl-4-nitroaniline

Procedure

Analogously to Example 7a), from 50 g. 2-methyl-4-nitroaniline is prepared 81.3 g. (88% of theory) N-benzyloxycarbonyl-2-methyl-4-nitroaniline which is reduced with sodium dithionite to give 44 g. 4-benzyloxycarbonylamido-3-methylaniline; m.p. 60°-62° C.

Workup

  1. customto give 44 g

Sources & evidence

ORD record
ord-377ad632f5eb489aaf574b5385a75816
Source dataset
uspto-grants-1993_03
Patent number
US05190862

Reaction notes

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