Methanol → Methyl 4-amino-5-chloro-2-methoxybenzoate

HRID 1465127Notes

Reaction equation

HRID 1465127 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 816264-Amino-5-chloro-2-methoxybenzoic acid

Product 1

HCID 700493Methyl 4-amino-5-chloro-2-methoxybenzoate

Procedure

To a solution of 4-amino-5-chloro-2-methoxybenzoic acid (20.0 g, 99.2 mmol) in methanol (250 mL) was added thionyl chloride (7.2 mL, 99.2 mmol). The reaction was refluxed for 16 h then concentrated in vacuo. Purification by silica gel chromatography (0-90% ethyl acetate/hexanes) provided methyl 4-amino-5-chloro-2-methoxybenzoate (21.3 g, quantitative yield). LC/MS m/z 216.3 [M+H]+.

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. concentrationthen concentrated in vacuo
  3. customPurification by silica gel chromatography (0-90% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-244c39a0a78a406b801a83830a42c7cf
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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