Thionyl Chloride → 7-Benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 2077253ノート

反応式

HRID 2077253 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7](CC2C=CC(OC)=CC=2OC)[CH2:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2].S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 671104847-Benzyloxy-2-(2,4-dimethoxy-benzyl)-4-hydroxy-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 671103537-Benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester収率 69.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dichloromethane (100 mL) was cooled to 0° C. and 5.7 g (12 mmol) of 7-benzyloxy-2-(2,4-dimethoxy-benzyl)-4-hydroxy-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl ester and 1.31 mL (18 mmol) of thionyl chloride were added. The reaction was stirred for one hour and then allowed to warm to room temperature and stirred for an additional 3 hours. 60 mL of hexanes was added to the resultant slurry and the white solid was collected by filtration through a medium glass fritted filter. The solid was partitioned between ethyl acetate and saturated sodium bicarbonate solution and the organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (2.7 g, white solid); MS (ESI+): 324.3 e/z (M+1)

後処理

  1. stirringstirred for an additional 3 hours
  2. filtrationthe white solid was collected by filtration through a medium glass fritted filter
  3. customThe solid was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. washthe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e9b0b445d8be40f893b338443ec536cf
出典データセット
uspto-grants-2011_04
特許番号
US07928120B2

反応ノート

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