p-Toluidine → 4-Aminobenzaldehyde

HRID 379361Notes

Reaction equation

HRID 379361 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.NC1C=CC=C2C(N(O)C(=O)C=12)=[O:14].[OH-].[Na+]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7813p-ToluidineHCID 14798Sodium HydroxideHCID 108884723-amino-N-hydroxyphthalimide

Product 1

HCID 111584-AminobenzaldehydeYield 62%

Procedure

172 mg (1.60 mmol) of 4-toluidine were reacted analogously to Example 1 in the presence of 32.1 mg (0.180 mmol) of 3-amino-N-hydroxyphthalimide. After a reaction time of 22 hours, the reaction solution was brought to pH 8 with 2M NaOH, extracted with chloroform and examined by NMR spectroscopy. Yield 62% of 4-aminobenzaldehyde.

Workup

  1. customAfter a reaction time of 22 hours
  2. extractionextracted with chloroform

Sources & evidence

ORD record
ord-88309852da3943ec8314dc8d6a8b2fe7
Source dataset
uspto-grants-2001_10
Patent number
US06297403B1

Reaction notes

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