Thiophene → 4-Amino-alpha-(4-chlorophenyl)-2-methoxybenzeneacetonitrile

HRID 1165840Notes

Reaction equation

HRID 1165840 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=2[O:20][CH3:21])[C:9]#[N:10])=[CH:4][CH:3]=1.S1C=CC=C1.[H][H]>CO.[Pt]>[NH2:17][C:14]1[CH:15]=[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]([O:20][CH3:21])[CH:13]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 23035215alpha-(4-Chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 230351864-Amino-alpha-(4-chlorophenyl)-2-methoxybenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 8.1 parts of α-(4-chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile, 2 parts of a solution of thiophene in methanol 4% and 200 parts of methanol is hydrogenated at normal pressure and at 50° C. with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is stirred in a small amount of 2-propanol. The product is filtered off and dried, yielding 4-amino-α-(4-chlorophenyl)-2-methoxybenzeneacetonitrile.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated in vacuo
  3. filtrationThe product is filtered off
  4. customdried

Sources & evidence

ORD record
ord-dafbacbf10e84f508f097fc1bc633d90
Source dataset
uspto-grants-1990_03
Patent number
US04912106

Reaction notes

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