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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 555499
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HRID 555499 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 31374Dimethylacetamide용매

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온도
155 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9430c5189ac24ea88b54977fd6aaffcd
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08053440B2

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