Sodium Hydroxide → 4-Methoxy-2-nitroaniline

HRID 1683161Notes

Reaction equation

HRID 1683161 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][C:9]=1[NH:10]C(=O)C)([O-:3])=[O:2].[OH-].[Na+]>>[N+:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 670752'-Nitro-p-acetanisidide

Product 1

HCID 667934-Methoxy-2-nitroanilineYield 95%

Procedure

To a 200 mL flask equipped with reflux condenser, thermometer, and stirring bar was added 3-nitro-4-acetylamino-1-methoxybenzene (22 g., 0.11 mole), 34.4 mL of 10% aqueous alcoholic sodium hydroxide. The stirring mixture produced the precipitation of red solid over 3 hours. The precipitate was filtered and washed with ice water and recrystallized from MeOH to give 3-nitro-4-amino-anisole (16.8 g., 95% yield, m.p. 123°-124° C.). Spectral characterizations of these materials were identical with literature information. Kim, et al., J. Korean Chem. Soc., 1987, 31: 464-470.

Workup

  1. customTo a 200 mL flask equipped
  2. temperaturewith reflux condenser
  3. customThe stirring mixture produced
  4. customthe precipitation of red solid over 3 hours
  5. filtrationThe precipitate was filtered
  6. washwashed with ice water
  7. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-9d915653f4cb44969ca69d9199626752
Source dataset
uspto-grants-1997_06
Patent number
US05637591

Reaction notes

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