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

HRID 409328ノート

反応式

HRID 409328 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 fitted 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
  3. customfitted
  4. filtrationfilter
  5. customThe solid was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. washthe organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-5608c88c89f54e978f3461e9d5cd92b5
出典データセット
uspto-grants-2014_06
特許番号
US08759373B2

反応ノート

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