Hydrochloric Acid → 4-Hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

HRID 523760ノート

反応式

HRID 523760 の反応式
[Na].[CH3:2][O:3][C:4](=[O:18])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([I:16])[CH:12]=2)[C:7]1=[O:17].[O-][CH2:20][CH2:21][CH2:22]C.[Na+].Cl>C(O)CCC>[CH2:2]([O:3][C:4]([C:5]1[NH:6][C:14](=[O:15])[C:13]2[C:8]([C:7]=1[OH:17])=[CH:9][CH:10]=[C:11]([I:16])[CH:12]=2)=[O:18])[CH2:20][CH2:21][CH3:22]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 23669364Sodium n-butylateHCID 66712568(5-Iodo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid methyl ester

生成物 1

HCID 667132364-Hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒2 回

反応条件

温度
80 °C

実験手順

Freshly cut sodium metal, 0.40 g, was dissolved in 22 ml of n-butanol at 65° C. under a nitrogen atmosphere. A mixture of 3.0 g of (5-iodo-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid methyl ester in 22 ml of n-butanol was added to the sodium butoxide solution and the reaction mixture was heated to 80° C. for 2 h. The cooled reaction mixture was acidified with 100 ml of 1M hydrochloric acid to give a solid precipitate. The solid was collected by filtration and separated by silica gel chromatography (eluant; 19:1 dichloromethane:ethyl acetate) to give 0.219 g of 4-hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester: MS-(−)-ion, M−1=386.0 amu, and 0.150 g of 4-hydroxy-6-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester: MS-(−) ion, M−1=386.0 amu.

後処理

  1. customThe cooled reaction mixture
  2. customto give a solid precipitate
  3. filtrationThe solid was collected by filtration
  4. customseparated by silica gel chromatography (eluant; 19:1 dichloromethane:ethyl acetate)

出典と根拠

ORDレコード
ord-e4f1687606e149c9b92beb296d1b9415
出典データセット
uspto-grants-2016_05
特許番号
US09339527B2

反応ノート

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