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

HRID 523761노트

반응식

HRID 523761 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1c7ab3e95f8c4682ad6add1466912483
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339527B2

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