Tetraethyltin → 2-Ethyl-4,6-dinitroaniline

HRID 429582

Reaction equation

HRID 429582 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7](Br)[C:5]=1[NH2:6])([O-:3])=[O:2].[CH2:15]([Sn](CC)(CC)CC)[CH3:16]>CN(C=O)C>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([CH2:15][CH3:16])[C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11704TetraethyltinHCID 157522-Bromo-4,6-dinitroaniline

Product 1

HCID 183798092-Ethyl-4,6-dinitroanilineYield 52.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-dinitro-6-bromoaniline (1.6 g, 6.1 mmol), tetraethyltin (2.4 ml, 12.2 mmol) and Cl2Pd(PPh3)2 (100 mg) in 10 ml of DMF was stirred at 140° C. for 12 h. Reaction mixture was concentrated in vacuc, yielding an oil which was purified on silica gel column chromatography (CH2Cl2, neat) to provide 0.68 g (3.2 mmol, 33%) of 2,4-dinitro-6-ethylaniline, which was converted to the diamine (0.45 g, 95%) on hydrogenation (H2/Pd—C).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuc
  3. customyielding an oil which
  4. customwas purified on silica gel column chromatography (CH2Cl2, neat)

Sources & evidence

ORD record
ord-0b40f1e8e00d4e748d72a58cfa76ccee
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Linked notes

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