Phosphorus oxybromide → HCID 86617067, compound

HRID 409221Notes

Reaction equation

HRID 409221 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][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:31])=O>CC#N>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:31])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178450850HCID 178450850, compound

Product 1

HCID 86617067HCID 86617067, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(2,6-Dimethyl-phenoxy)-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (4 mmol, 1.53 g), POBr3 (16 mmol, 4.63 g), MeCN (30 mL) was refluxed gently with stirring before it was concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL). To the solution was added NaHCO3 (20 g) and then water (100 mL) in small portions with stirring. The mixture was stirred for 1 h at ambient temperature before the organic phase was separated and dried over MgSO4. Concentration and purification of the residue by flash column chromatography on silica gel using CH2Cl2 as the eluent gave the title compound as a yellowish oil (640 mg); MS-(+)-ion: M+1, 79Br/81Br=443.9 and 445.9.

Workup

  1. temperaturewas refluxed gently
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  4. additionTo the solution was added NaHCO3 (20 g)
  5. stirringwater (100 mL) in small portions with stirring
  6. stirringThe mixture was stirred for 1 h at ambient temperature before the organic phase
  7. customwas separated
  8. dry with materialdried over MgSO4
  9. concentrationConcentration and purification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-51d6944c3bb84e92856f53819e8ae3a1
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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