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

HRID 250498Notes

Reaction equation

HRID 250498 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=CC2C(C=1O)=CC=C(OC1C=CC(OC)=CC=1)C=2)=O)CCC.P(Br)(Br)([Br:56])=O>C(#N)C>[Br:56][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 667126187-(4-Methoxy-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterHCID 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 D-1 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-b6b10c408cad452990f014bddef9263a
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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