Hydrochloric Acid → 1,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 523711

反応式

HRID 523711 の反応式
[Na].[CH2:2]([O:6][C:7](=[O:20])[CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19])[CH2:3][CH2:4][CH3:5].Cl>C(O)CCC>[CH2:2]([O:6][C:7]([C:8]1[N:9]=[C:10]([OH:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:20])[CH2:3][CH2:4][CH3:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 357739(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl esterHCID 5360545Sodium2 回

生成物 1

HCID 1784508431,4-Dihydroxy-isoquinoline-3-carboxylic acid butyl ester収率 73.9%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒2 回

実験手順

4.41 g of sodium (190 mmol) were dissolved in 250 ml of n-butanol with stirring. After the sodium was completely dissolved the solution was allowed to cool to ambient temperature and a solution of 24.0 g (91.9 mmol) of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid butyl ester in 150 ml of butanol was added with stirring. The solution was heated to 100° C. within 30 min and stirred at this temperature for 1 h. Then the mixture was allowed to cool to ambient temperature and was stored at ambient temperature for 18 h. Then the pH of the mixture was adjusted to 2 to 3 by the addition of aqueous 2N hydrochloric acid with stirring. Stirring was continued for 30 min before the solid component was filtered by suction. The filter cake was washed thoroughly with water, and dried in vacuo at 50° C. to give a white solid. 17.75 g of the title compound were obtained; MS-(+)-ion: M+1=262.1.

後処理

  1. stirringwith stirring
  2. temperatureThe solution was heated to 100° C. within 30 min
  3. stirringstirred at this temperature for 1 h
  4. temperatureto cool to ambient temperature
  5. stirringwith stirring
  6. stirringStirring
  7. waitwas continued for 30 min before the solid component
  8. filtrationwas filtered by suction
  9. washThe filter cake was washed thoroughly with water
  10. customdried in vacuo at 50° C.
  11. customto give a white solid

出典と根拠

ORDレコード
ord-706ba94e06654bef861f5a5cf0937dec
出典データセット
uspto-grants-2016_05
特許番号
US09339527B2

関連ノート

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