Ammonium Chloride → HCID 21483136, compound

HRID 1415582Notes

Reaction equation

HRID 1415582 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C:12]#[N:13]>[Fe].CC1C=CC=CC=1>[ClH:3].[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH:11]([C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=2[Cl:3])[C:12]#[N:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21483200HCID 21483200, compound

Product 1

HCID 21483136HCID 21483136, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

20 parts of iron-powder are added to 190 parts of ammonium chloride solution 0.78N at reflux temperature. Then there is added dropwise a solution of 20 parts of 2,4-dichloro-α-(4-nitrophenyl)benzeneacetonitrile in 180 parts of methylbenzene. Upon completion, stirring is continued overnight at reflux. The reaction mixture is cooled at 60° C and filtered over hyflo. The filter-cake is washed with tetrahydrofuran. The filtrate is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2,2'-oxybispropane, methanol and 2-propanol. The salt is filtered off and dried, yielding α-(4-aminophenyl)-2,4-dichlorobenzeneacetonitrile hydrochloride; mp. 207.2° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux
  3. filtrationfiltered over hyflo
  4. washThe filter-cake is washed with tetrahydrofuran
  5. customThe filtrate is dried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customdried

Sources & evidence

ORD record
ord-c4151cd7f23748f8986b155b540700d7
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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