Ammonia → 4-Amino-3-methyl-5-nitrobenzonitrile

HRID 1767008Notes

Reaction equation

HRID 1767008 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([NH:12]C(=O)C(F)(F)F)=[C:5]([CH3:19])[CH:4]=1)#[N:2].N>CO>[NH2:12][C:6]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[CH3:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22021502n-(4-Cyano-2-methyl-6-nitro-phenyl)-2,2,2 trifluoro-acetamide

Product 1

HCID 220210074-Amino-3-methyl-5-nitrobenzonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-cyano-2-methyl-6-nitro-phenyl)-2,2,2-trifluoro-acetamide (5 g, 18.3 mmol) and 2 M ammonia in methanol (80 mL) was heated to reflux for 14 h and then cooled to room temperature. After concentration in vacuo, the residue was purified by flash chromatography (20% EtOAc/hexane) to yield the title compound (3.24 g, 100%, ca 80% pure). 1H NMR (300 MHz, CDCl3) δ 8.40 (1H, s), 7.47 (1H, s), 6.6-6.8 (2H, broad s), 2.89 (3H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 h
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-e797a696d58941059b1cb0e3a9827427
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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