Acetic Acid → 4-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

HRID 250330Notes

Reaction equation

HRID 250330 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].I.C(O)(=O)C>C(OCC)(=O)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24841Hydrogen iodideHCID 865954621-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667130924-Hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl esterYield 34.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 432 mg of 1-bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (1 mmol), 63 mg of red phosphorous (2 mmol), 0.4 ml of aqueous 57 wt % HI (3 mmol), and 1 ml of glacial acetic acid was refluxed with stirring for 30 min. Then the reaction mixture was diluted with 25 ml of ethyl acetate, filtered by suction through a pad of celite, washed with a solution of 0.2 g of NaHSO3 in 5 ml of water, and washed two times with 5 ml of concentrated aqueous sodium bicarbonate solution. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexanes: ethyl acetate (85:15). 123 mg of the title compound were obtained; 1H NMR (CDCl3): δ=11.85 (s, 1H), 8.60 (s, 1H), 8.23 (d, 1H), 7.38 to 7.63 (m, 7H), 4.49 (t, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 0.98 (t, 3H).

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered by suction through a pad of celite
  3. washwashed with a solution of 0.2 g of NaHSO3 in 5 ml of water
  4. washwashed two times with 5 ml of concentrated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with hexanes: ethyl acetate (85:15)

Sources & evidence

ORD record
ord-5ef056db01b344e1bab49b9e917f0984
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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