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

HRID 1793966Notes

Reaction equation

HRID 1793966 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>>[CH3:18][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=1[O:12][CH3:13]

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

Conditions

Temperature
0 °C

Procedure

4-Amino-5-chloro-2-methoxy benzoic acid (50.0 g, 248 mmol) was suspended in methanol (500 mL) and the slurry cooled to 0° C. Thionyl chloride (54.3 mL, 744 mmol) was then added dropwise over the course of 20 minutes. Initially, a clear solution formed, which subsequently turned to a white suspension. The reaction was warmed to room temperature and stirred for 3 hours. The solvent was evaporated and the resulting slurry suspended in diethyl ether (1 L). The solid was filtered and rinsed thoroughly with diethyl ether to afford the title compound (50.9 g) as the hydrochloride salt. The salt was suspended in 1 N sodium hydroxide and stirred vigorously for 30 minutes. Filtration and thorough rinsing with water afforded the free base as a white solid, m.p. 136–137° C.

Workup

  1. customInitially, a clear solution formed
  2. temperatureThe reaction was warmed to room temperature
  3. customThe solvent was evaporated
  4. filtrationThe solid was filtered
  5. washrinsed thoroughly with diethyl ether

Sources & evidence

ORD record
ord-58dacb2d8d2149a2b9bf9101f01f4e77
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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