Phosphorus oxybromide → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

HRID 1866311Notes

Reaction equation

HRID 1866311 reaction equation
C([O:5][C:6]([C:8]1[N:9]=[C:10](O)[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])CCC.C(OC(C1N=C(O)C2C(C=1O)=CC=C(OC1CCCCC1)C=2)=O)CCC.P(Br)(Br)([Br:55])=O>C(#N)C>[Br:55][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([OH:5])=[O:7])[N:9]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 178450857HCID 178450857, compoundHCID 178450860HCID 178450860, compound

Product 1

HCID 860145681-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,4-Dihydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (Example A-63 d) Compound A) (29.0 g) and phosphorous oxybromide (67.5 g) in 600 ml anhydrous acetonitrile was stirred at reflux for 4 hours. After cooling the reaction mixture was concentrated and saturated sodium bicarbonate solution and ethyl acetate were added to the residue and stirred overnight. Precipitate that formed between layers was collected and washed with water to give the title compound (10.2 g). MS-(+)-ion M+1=376.0, 378.1.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling the reaction mixture
  3. concentrationwas concentrated
  4. additionsaturated sodium bicarbonate solution and ethyl acetate were added to the residue
  5. customPrecipitate that formed between layers
  6. customwas collected
  7. washwashed with water

Sources & evidence

ORD record
ord-2c15affa0cbb4c21a9ec35b01f26543d
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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