Methanol → Methyl 3-aminophenylacetate

HRID 491536

反応式

HRID 491536 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 13054266Methyl 3-aminophenylacetate

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5490efe37fbc4a6b8c5795ef65309bf1
出典データセット
uspto-grants-2009_05
特許番号
US07531556B2

関連ノート

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