Water → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

HRID 1406149Notes

Reaction equation

HRID 1406149 reaction equation
P(Br)(Br)([Br:3])=O.[CH2:6]([O:10][C:11]([C:13]1[N:14]=[C:15](O)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]=2)=[O:12])[CH2:7][CH2:8][CH3:9].C(=O)(O)[O-].[Na+].O>C(#N)C>[CH2:6]([O:10][C:11]([C:13]1[N:14]=[C:15]([Br:3])[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]=2)=[O:12])[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178450860HCID 178450860, compound

Product 1

HCID 865954621-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl esterYield 68.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4.59 g of phosphorous oxybromide (16 mmol) in 25 ml of anhydrous acetonitrile were added 1.108 g of 1,4-dihydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (3 mmol) and the mixture was refluxed gently with stirring for 1 h. Then 5.04 g of sodium bicarbonate (60 mmol) were added, followed by the dropwise addition of 8 ml of water. After stirring at ambient temperature for 90 min the mixture was concentrated in vacuo to about one third of its volume, 40 ml of water were added and the mixture was extracted with 30 ml of ethyl acetate. The mixture was filtered by suction. The organic phase was separated, dried over MgSO4, and filtered through a pad of silica gel. Evaporation in vacuo gave 0.885 g of the title compound; 1H NMR (CDCl3): δ=11.84 (s, 1 H), 8.21 (d, 1 H), 7.91 (d, 1 H), 7.40 to 7.55 (m, 6 H), 4.46 (t, 2 H), 1.84 (m, 2 H), 1.48 (m, 2 H), 0.98 (t, 3 H).

Workup

  1. temperaturethe mixture was refluxed gently
  2. stirringAfter stirring at ambient temperature for 90 min the mixture
  3. concentrationwas concentrated in vacuo to about one third of its volume, 40 ml of water
  4. additionwere added
  5. extractionthe mixture was extracted with 30 ml of ethyl acetate
  6. filtrationThe mixture was filtered by suction
  7. customThe organic phase was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered through a pad of silica gel
  10. customEvaporation in vacuo

Sources & evidence

ORD record
ord-d8a428de23d143f3883133c5ef7926d1
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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