Acrylic Acid → N-(2-acetyl-4,5-dimethoxyphenyl)-beta-alanine

HRID 236622

反応式

HRID 236622 の反応式
[CH3:1][C:2]([C:4]1[C:9]([NH2:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1)=[O:3].[C:15]([OH:19])(=[O:18])[CH:16]=[CH2:17]>C(O)(=O)C>[C:2]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([O:11][CH3:12])=[CH:8][C:9]=1[NH:10][CH2:17][CH2:16][C:15]([OH:19])=[O:18])(=[O:3])[CH3:1]

参加物

4

反応物 2

HCID 6581Acrylic AcidHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-

生成物 1

HCID 13773235N-(2-acetyl-4,5-dimethoxyphenyl)-beta-alanine収率 84.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-amino-4,5-dimethoxyacetophenone (910 g, 4.66 mol), acrylic acid (730 ml., 10.67 mol), and acetic acid (2100 ml) was heated at 90° C. for 2 hours. Following treatment with Darco and hot filtration, the product was precipitated by the addition of water (2475 ml) over a 1 hour period. The reaction mixture was cooled and the product was filtered and washed with cold distilled water (4×90 ml) and cold methanol (1×600 ml). Drying under vacuum at 60° C. gave 1049 g (84%) of the product as a yellow powder, mp 149.5°-151.5° C. NMR (CDCl3) δ 2.50 (s, 3H, ArCOCH3), 2.73 (t, 2H, CH2 --CO2H), 3.57 (t, 2H, N--CH2), 3.82 (s, 3H, CH3OAr), 3.93 (s, 3H, CH3OAr), 6.18 (s, 1H, ArH), 7.13 (s, 1H, ArH), 10.05 (broad s, 2H, NH, COOH).

後処理

  1. filtrationwith Darco and hot filtration
  2. customthe product was precipitated by the addition of water (2475 ml) over a 1 hour period
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe product was filtered
  5. washwashed
  6. distillationwith cold distilled water (4×90 ml) and cold methanol (1×600 ml)
  7. customDrying under vacuum at 60° C.

出典と根拠

ORDレコード
ord-89a52b8ed6fa4896af039e39adf85f21
出典データセット
uspto-grants-1987_02
特許番号
US04645836

関連ノート

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