Methanol → Methyl 2-amino-4-methylbenzoate

HRID 574315

Reaction equation

HRID 574315 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:7]=1[NH2:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 753164-Methylanthranilic acid

Product 1

HCID 11205965Methyl 2-amino-4-methylbenzoateYield 82%

Procedure

Concentrated sulphuric acid (1 mL) was added to a solution of 2-amino-4-methyl-benzoic acid (1.0 g, 6.62 mmol) in dry methanol (10 mL) at 0° C., and then heated at reflux for 16 hr. The mixture was cooled to room temperature and concentrated in vacuo. The crude compound was diluted with water (25 mL) and basified with sodium bicarbonate (10 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with water (50 mL), brine (50 mL) and dried over sodium sulfate. The organic layer was concentrated under reduced pressure affording 2-amino-4-methyl-benzoic acid methyl ester (900 mg, 82%) as yellow liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. concentrationconcentrated in vacuo
  4. additionThe crude compound was diluted with water (25 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  6. washthe combined organic layers were washed with water (50 mL), brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7a055b4162445569208edc4dad34a54
Source dataset
uspto-grants-2015_05
Patent number
US09034887B2

Linked notes

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