Methanol → Methyl 5-Amino-2-chlorobenzoate

HRID 1992229Notes

Reaction equation

HRID 1992229 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 378795-Amino-2-chlorobenzoic acid

Product 1

HCID 5200412Methyl 5-Amino-2-chlorobenzoateYield 95%

Procedure

To a solution of 5-amino-2-chlorobenzoic acid (6.0 g, 35 mmol) in anhydrous methanol (100 ml) was added dropwise thionyl chloride (15 ml) with stirring under a nitrogen atmosphere. After stirring for 3 hours the volatiles were removed by spin evaporation in vacuo and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate and then water. The organic layer was concentrated by spin evaporation in vacuo with the addition of dichloromethane (3 times) to give methyl 5-amino-2-chlorobenzoate as a white solid (6.2 g, 95%). 1H-NMR (400 MHz, DMSO-d6): δ 7.20-7.14 (m, 1H), 7.13-7.02 (m, 1H), 6.73-6.67 (m. 1H), 3.89 (s, 3H). ES-LCMS m/z 186 (M+H).

Workup

  1. stirringAfter stirring for 3 hours the volatiles
  2. customwere removed by spin evaporation in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate
  5. concentrationThe organic layer was concentrated by spin evaporation in vacuo with the addition of dichloromethane (3 times)

Sources & evidence

ORD record
ord-1589a5c4d28947b49e46925dfecc3f86
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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