Methanol → Methyl 3-aminophenylacetate

HRID 491536

반응식

HRID 491536 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:16])=[O:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 571807(3-Aminophenyl)acetic acid

생성물 1

HCID 13054266Methyl 3-aminophenylacetate

반응 조건

온도
0 °C

실험 절차

3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0° C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise while stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4) to afford methyl 3-aminophenylacetate as a brown oil. (14.1 g, 83%). 1H NMR (CDCl3) δ 7.12 (1H, dd), 6.7-6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s).

후처리

  1. customA clear orange solution was obtained
  2. stirringwhich was stirred for 4 hours
  3. customevaporated
  4. customThe solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL)
  5. washthe organic phase washed with saturated sodium bicarbonate (100 mL), and brine
  6. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-5490efe37fbc4a6b8c5795ef65309bf1
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531556B2

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