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

HRID 908794Notes

Reaction equation

HRID 908794 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3d4c3b1ec1384a1cac98c8e4371017fa
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

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