Chloroacetonitrile → 2-(2-Amino-2-oxoethoxy)-5-chlorobenzoic acid

HRID 1888671Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].C(=O)([O-])[O-:14].[K+].[K+].Cl[CH2:20][C:21]#[N:22].[OH-].[Na+]>>[NH2:22][C:21](=[O:14])[CH2:20][O:12][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

Reactant 4

HCID 7856Chloroacetonitrile

HCID 11430Potassium Carbonate

HCID 14798Sodium Hydroxide

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 87073112-(2-Amino-2-oxoethoxy)-5-chlorobenzoic acid

Procedure

Commercially available, methyl 5-chloro-2-hydroxybenzoate (Maybridge), potassium carbonate, 2-chloroacetonitrile (Aldrich) and sodium hydroxide were processed according to the method described for Example 130A to obtain the title compound. MS (ESI+) m/z 248 (M+H2O)+.

Sources & evidence

ORD record: ord-921c8b08d33546499270031f04403cbf
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501794B2

Reaction notes

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