Phosphorus oxychloride → HCID 86014573, compound

HRID 250405Notes

Reaction equation

HRID 250405 reaction equation
[CH2:1]([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]([Br:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:23])=O>C(#N)C>[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]([Br:19])[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178450840HCID 178450840, compound

Product 1

HCID 86014573HCID 86014573, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

170 mg (0.5 mmol) of 7-bromo-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (from Example D-21 c) was dissolved in 2 ml of anhydrous acetonitrile. Phosphorous oxychloride (536 mg, 3.5 mmol) was added and the resulting mixture was stirred at reflux for 4 h. After cooling, the mixture was concentrated and the residue was taken into ethyl acetate. Ethyl acetate mixture was poured into saturated sodium bicarbonate solution with efficient stirring for 1 h. Two phases were separated. Aqueous layer was extracted with ethyl acetate. Combined organic layer was dried over magnesium sulfate, filtered and concentrated. Crude product was purified by silica gel chromatography eluting with methylene chloride to give 78 mg of product as white solid. MS-(+)-ion: M+1=359.96, 357.98

Workup

  1. temperatureat reflux for 4 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. additionEthyl acetate mixture was poured into saturated sodium bicarbonate solution
  5. stirringwith efficient stirring for 1 h
  6. customTwo phases were separated
  7. extractionAqueous layer was extracted with ethyl acetate
  8. dry with materialCombined organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customCrude product was purified by silica gel chromatography
  12. washeluting with methylene chloride

Sources & evidence

ORD record
ord-29bb3b3bea3746ce97a5baacec282d4c
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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