Phosphorus oxybromide → HCID 89813158, compound

HRID 1481194Notes

Reaction equation

HRID 1481194 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[CH:9][CH:10]=2)[C:5]([OH:20])=[C:4]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[N:3]=1.P(Br)(Br)([Br:30])=O>C(#N)C>[Br:30][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[CH:9][CH:10]=2)[C:5]([OH:20])=[C:4]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[N:3]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178450849HCID 178450849, compound

Product 1

HCID 89813158HCID 89813158, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of butyl 1,4-dihydroxy-6-(o-tolyloxy)isoquinoline-3-carboxylate (1.5 g, 4.2 mmol) and POBr3 (4.9 g, 16.8 mmol) in acetonitrile (32 mL) was heated to reflux for 90 minutes. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in CHCl3 (200 mL) and to the solution were added NaHCO3 (10 g) and H2O (13 mL). The resulting mixture was stirred vigorously at room temperature for 30 minutes before dried over MgSO4. The mixture was then filtered and the filtrate was concentrated in vacuo and then purified by flash chromatography (0-10% EtOAc/CH2Cl2) to give the title compound in 0.9 g. 1H NMR (CDCl3, 200 MHz): δ=11.74 (s, 1H), 8.21 (d, 1H, J=8.4 Hz), 7.52-7.44 (m, 2H), 7.34-7.15 (m, 3H), 7.03 (d, 1H, J=8.8 Hz), 4.46 (t, 2H, J=7.2 Hz)), 2.20 (s, 3H), 1.92-1.77 (m, 2H), 1.56-1.38 (m, 2H), 0.98 (t, 3H, J=7.2 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 minutes
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in CHCl3 (200 mL) and to the solution
  5. additionwere added NaHCO3 (10 g) and H2O (13 mL)
  6. dry with materialbefore dried over MgSO4
  7. filtrationThe mixture was then filtered
  8. concentrationthe filtrate was concentrated in vacuo
  9. custompurified by flash chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-36806c64b78d44a688afa08179fb6960
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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