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p-Toluenesulfonic acid → 3-[4-(5,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenyl]-propionic acid ethyl ester

HRID 336703
ノート
印刷プレビュー

反応式

HRID 336703 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[CH2:15]([O:17][C:18](=[O:29])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1)[CH3:16].S(=O)(O)[O-].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.CN(C)C(=O)C>[CH2:15]([O:17][C:18](=[O:29])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)=[CH:25][CH:26]=1)[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 12169276Ethyl 3-(4-formylphenyl)propanoateHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

生成物 1

HCID 1363988553-[4-(5,7-Dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenyl]-propionic acid ethyl ester収率 97%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
155 °C

実験手順

To a round-bottomed flask were added 2-amino-4,6-dimethoxy-benzamide (0.161 g, 0.82 mmol), 3-(4-formyl-phenyl)-propionic acid ethyl ester (0.170 g, 0.82 mmol), sodium bisulfite (0.160 g, 0.902 mmol), p-toluenesulfonic acid (0.016 g, 0.082 mmol) and N,N-dimethylacetamide (10 mL). The reaction mixture was refluxed at 155° C. for 16 h before being cooled to room temperature. Water was added and the precipitated solid was filtered off and washed with water and methanol to obtain 3-[4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenyl]-propionic acid ethyl ester (0.304 g, 97%). The compound 3-[4-(5,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenyl]-propionic acid ethyl ester (0.304 g, 0.795 mmol) was taken up in a 1:1 mixture of THF and methanol (6 mL). A solution of potassium hydroxide (0.089 g, 1.59 mmol) in water (6 mL) was added to the reaction mixture and stirred at room temperature for 16 h. The solvent was removed and the reaction mixture was acidified with 1 N hydrochloric acid. The precipitated solid was filtered off and washed with water and methanol. The solid was further washed with methanol to obtain 3-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)propanoic acid (0.143 g, 51%). Selected data: MS (ES) m/z: 355.0; MP 250.6-251.1° C.

後処理

  1. temperaturebefore being cooled to room temperature
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water and methanol

出典と根拠

ORDレコード
ord-fab883717b2d434fb2201de619719a80
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889698B2

反応ノート

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