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3,4-Dichlorobenzyl chloride → 2-(3,4-Dichlorobenzyl)-1,2-dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

HRID 894391
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HRID 894391 반응식
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6](=[O:18])[C:7]2[C:12]([C:13]=1[CH2:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=2.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23]Cl>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][N:5]1[C:4]([CH3:3])=[C:13]([CH2:14][C:15]([OH:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:18]
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참가 물질

5

반응물 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 127155091,2-Dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

생성물 1

HCID 127155122-(3,4-Dichlorobenzyl)-1,2-dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (48 mg., 2.0 mmol) (Ventron, washed free of mineral oil with hexane) and 2 ml. dimethylformamide were reacted with 1,2-dihydro-3-methyl-1-oxo-4-isoquinoline acetic acid (217 mg., 1.0 mmol). After homogeneity was observed, 3,4-dichlorobenzyl chloride (196 mg., 1.0 mmol) in 1 ml. dimethylformamide was added. The mixture was heated at 110° for 3 hr, cooled and partitioned between hydrochloric acid and ethyl acetate. The crude product obtained from the organic layer after several aqueous washings, drying over magnesium sulfate, filtration, and vacuum evaporation was column chromatographed on silica gel with ethyl acetate; 104 mg., 28%, mp 218°-220°.

후처리

  1. temperatureThe mixture was heated at 110° for 3 hr
  2. temperaturecooled
  3. custompartitioned between hydrochloric acid and ethyl acetate

출처 및 근거

ORD 기록
ord-20d21f62612741e2a9455abbb68e36e2
출처 데이터셋
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04283539

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