Sodium Hydroxide → 4-Neopentyl-2-nitroaniline

HRID 1424227Notes

Reaction equation

HRID 1424227 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+]>O>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 85802767N-(4-Neopentyl-2-nitrophenyl)acetamide

Product 1

HCID 858027694-Neopentyl-2-nitroanilineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of N-(4-neopentyl-2-nitrophenyl)acetamide (Preparation 87, 3.0 g, 12.0 mmol) in aqueous sodium hydroxide (6.0 M, 20 mL, 120 mmol) was heated at 90° C. for 36 hours. After cooling, a small amount of water was added and the mixture extracted with dichloromethane (5×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo to provide the title compound (2.15 g, 90%) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with dichloromethane (5×)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f4e2452d9f24f978c3e2aaab21f9e55
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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