Methanol → Methyl 2-amino-4-methylbenzoate

HRID 574315

반응식

HRID 574315 반응식
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]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 753164-Methylanthranilic acid

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7a055b4162445569208edc4dad34a54
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034887B2

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