Ammonium Chloride → alpha-(4-Amino-2-chlorophenyl)-4-chloro-alpha-methylbenzeneacetonitrile

HRID 868305Notes

Reaction equation

HRID 868305 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[Cl:21])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.[Cl-].[NH4+]>[Fe].CC1C=CC=CC=1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]([CH3:11])([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]#[N:10])=[C:13]([Cl:21])[CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 137703554-Chloro-alpha-(2-chloro-4-nitrophenyl)-alpha-methylbenzeneacetonitrile

Product 1

HCID 13770357alpha-(4-Amino-2-chlorophenyl)-4-chloro-alpha-methylbenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 20 parts of 4-chloro-α-(2-chloro-4-nitrophenyl)-α-methylbenzeneacetonitrile, 7 parts of iron powder, 250 parts of ammonium chloride solution 0.78N and 200 parts of methylbenzene was stirred and refluxed for 3 hours. The reaction mixture was filtered hot. The aqueous phase was separated and washed with methylbenzene. The combined organic layers were washed successively with water, sodium hydrogen carbonate solution and again with water, dried and evaporated. The residue was washed with 1,1'-oxybisethane and dried, yielding 10 parts of α-(4-amino-2-chlorophenyl)-4-chloro-α-methylbenzeneacetonitrile; mp. 135.2° C. (intermediate 24).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe reaction mixture was filtered hot
  3. customThe aqueous phase was separated
  4. washwashed with methylbenzene
  5. washThe combined organic layers were washed successively with water, sodium hydrogen carbonate solution and again with water
  6. customdried
  7. customevaporated
  8. washThe residue was washed with 1,1'-oxybisethane
  9. customdried

Sources & evidence

ORD record
ord-957c83066f0544fe9a75fa5b38200709
Source dataset
uspto-grants-1988_10
Patent number
US04778887

Reaction notes

Loading…