Phosphorus oxychloride → 1-Chloro-4-hydroxy-7-iodo-isoquinoline-3-carboxylic acid butyl ester

HRID 250416ノート

反応式

HRID 250416 の反応式
[CH2:1]([O:5][C:6]([C:8]1[NH:9][C:10](=O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([I:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Cl:23])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([I:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 667132364-Hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester

生成物 1

HCID 860145321-Chloro-4-hydroxy-7-iodo-isoquinoline-3-carboxylic acid butyl ester

実験手順

0.215 g of 4-hydroxy-7-iodo-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid butyl ester were added to 5 ml of POCl3 at room temperature. The mixture was refluxed for 3 h and POCl3 was removed under vacuum. The residue was dissolved in ethyl acetate and the solution was washed with satd. aqueous sodium bicarbonate, dried (MgSO4), filtered, and concentrated to give 0.205 g of a while solid: Proton NMR (200 MHz, chloroform-d) δ 11.91 (s, 1H), 8.67 (m, 1H), 8.10 (m, 2H), 4.49 (t, J=7 Hz, 2H), 1.95-1.75 (m, 2H), 1.60-1.39 (m, 2H), 1.00 (t, J=7 Hz, 3H).

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. customPOCl3 was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with satd
  5. dry with materialaqueous sodium bicarbonate, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 0.205 g of a while solid

出典と根拠

ORDレコード
ord-dd9cca2b557945329888e06bef45eb9c
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

反応ノート

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