Tetramethyltin → HCID 22988665, compound

HRID 2186112Notes

Reaction equation

HRID 2186112 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].C[Sn](C)(C)C>CN(C=O)C>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:5]=2)[C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11661TetramethyltinHCID 157522-Bromo-4,6-dinitroaniline

Product 1

HCID 22988665HCID 22988665, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-dinitro-6-bromoaniline (2.5 g, 9.5 mmol), tetramethyltin (6.1 g, 14.3 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 vacuo, yielding an oil which was purified on silica gel column chromatography (CH2Cl2, neat) to provide 1.0 g (3.8 mmol, 41%) of 2,4-dinitro-6-phenylaniline, which was converted to the diamine (0.72 g, >95%) on hydrogenation (H2/Pd-C).

Workup

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

Sources & evidence

ORD record
ord-24f95c42657745d6a13f0bbc661e20cd
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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