Cyclopropylamine → 3-Bromo-4-(cyclopropylamino)-benzonitrile

HRID 1976793Notes

Reaction equation

HRID 1976793 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[CH:11]1([NH2:14])[CH2:13][CH2:12]1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:14][CH:11]1[CH2:13][CH2:12]1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 219987273-Bromo-4-(cyclopropylamino)-benzonitrileYield 118.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-bromo-4-fluorobenzonitrile (9.33 mmol) and cyclopropylamine (7.90 g, 136 mmol) in methanol (60 mL) was heated to 60° C. for 20 hours and concentrated. The concentrate was purified by flash column chromatography with 96:4 hexane/ethyl acetate to provide 2.63 g of the desired product. MS (ESI(+)) m/z 239 (M+H)+;

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography with 96:4 hexane/ethyl acetate

Sources & evidence

ORD record
ord-700ba7b8bd034fbcb97e708891bd9913
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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