Potassium Cyanide → 3-(4-Cyano-3-nitrobenzoyl)propionic acid

HRID 596699Notes

Reaction equation

HRID 596699 reaction equation
N[C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].N([O-])=O.[Na+].[C-:22]#[N:23].[K+]>Cl>[C:22]([C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])#[N:23]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 214321703-(4-Amino-3-nitrobenzoyl)propionic acidHCID 23668193Sodium Nitrite

Product 1

HCID 214502243-(4-Cyano-3-nitrobenzoyl)propionic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

i. 3-(4-Amino-3-nitrobenzoyl)propionic acid was diazotised in aqueous hydrochloric acid with sodium nitrite and the resultant solution treated with cuprous cyanide in potassium cyanide solution to give 3-(4-cyano-3-nitrobenzoyl)propionic acid, also available by a cyanide displacement reaction of 3-(4-fluoro-3-nitrobenzoyl)propionic acid.

Sources & evidence

ORD record
ord-17800858b5c045cc80ee7198d1908575
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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