Ammonium Chloride → 61437-85-2

HRID 1415585Notes

Reaction equation

HRID 1415585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:11]2[CH:16]=[C:15]([CH3:17])[C:14](=[N:18]O)[CH:13]=[C:12]2[Cl:20])[C:9]#[N:10])=[CH:4][CH:3]=1.[Cl-].[NH4+]>[Fe].CC1C=CC=CC=1>[NH2:18][C:14]1[C:15]([CH3:17])=[CH:16][C:11]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]#[N:10])=[C:12]([Cl:20])[CH:13]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 700544-Chloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadien-1-ylidene]benzeneacetonitrile

Product 1

HCID 272375261437-85-2

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 40 parts of 4-chloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadien-1-ylidene]benzeneacetonitrile, 50 parts of iron-powder, 1500 parts of ammonium chloride solution 0.78N and 270 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is filtered over hyflo and the filter-cake is washed with 4-methyl-2-pentanone. The filtrate is dried, filtered and evaporated. The solid residue is crystallized from methylbenzene. The product is filtered off and recrystallized from methylbenzene, yielding 4-amino-2-chloro-α-(4-chlorophenyl)-5-methylbenzeneacetonitrile; mp. 152.6° C.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture is filtered over hyflo
  3. washthe filter-cake is washed with 4-methyl-2-pentanone
  4. customThe filtrate is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue is crystallized from methylbenzene
  8. filtrationThe product is filtered off
  9. customrecrystallized from methylbenzene

Sources & evidence

ORD record
ord-126b345fdc694b8ebbc98f895108ff60
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

Loading…