Water → 4-Amino-3-fluorobenzonitrile

HRID 1589749Notes

Reaction equation

HRID 1589749 reaction equation
BrC1C=CC(N[F:7])=CC=1.[Cu][C:11]#[N:12].[CH2:13]([NH2:16])[CH2:14]N.O.CN1[CH2:23][CH2:22][CH2:21][C:20]1=O>>[NH2:16][C:13]1[CH:14]=[CH:20][C:21]([C:11]#[N:12])=[CH:22][C:23]=1[F:7]

Participants

6

Reactant 5

HCID 962WaterHCID 3301EthylenediamineHCID 13387N-methyl-2-pyrrolidoneHCID 19599807HCID 19599807, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 27564314-Amino-3-fluorobenzonitrile

Procedure

100 g (0.53 mol) of 4-bromo-fluoroaniline (manufactured by Aldorich Co.) and 70.8 g (0.79 mol) of copper (I) cyanide was refluxed in N-methyl-2-pyrrolidinone for three hours while stirring. The solution was cooled and a solution of 130 cm3 of ethylene diamine and 130 cm3 of water was added drop-wise while stirring. The solution was extracted three times with 200 cm3 of chloroform and sufficiently washed with water. The chloroform was distilled off and the residue was distilled under reduced pressure (150° C./9 mmHg) to yield 55 g (0.40 mol) of 4-amino-3-fluorobenzonitrile.

Workup

  1. temperatureThe solution was cooled
  2. stirringwhile stirring
  3. extractionThe solution was extracted three times with 200 cm3 of chloroform
  4. washsufficiently washed with water
  5. distillationThe chloroform was distilled off
  6. distillationthe residue was distilled under reduced pressure (150° C./9 mmHg)

Sources & evidence

ORD record
ord-45a0dd277acd44d4ae9927f380946f41
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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