Acetic Acid → HCID 20296017, compound

HRID 1389928Notes

Reaction equation

HRID 1389928 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(O)(=O)C.[C-:25]#[N:26].[K+]>O>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[C:25]#[N:26])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8635Methyl AnthranilateHCID 9032Potassium CyanideHCID 707414-Bromobenzaldehyde

Product 1

HCID 20296017HCID 20296017, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 17.4 parts of methyl 2-aminobenzoate 18.5 parts of 4-bromobenzaldehyde in 200 parts of glacial acetic acid is added dropwise a solution of 8.15 parts of potassium cyanide in 15 parts of water, while keeping the temperature below 16° C. Upon completion, stirring is continued for 19 hours at room temperature. The precipitated product is filtered off, washed with 2,2'-oxybispropane and dried in vacuo, yielding 25 parts of methyl 2-{[(4-bromophenyl)cyanomethyl]amino}benzoate; mp. 111.5° C.

Workup

  1. customthe temperature below 16° C
  2. filtrationThe precipitated product is filtered off
  3. washwashed with 2,2'-oxybispropane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c60fd1d9ada84e72ab0ce8e5ea3bcb88
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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