Sodium Carbonate → 1,2-Dihydro-4-[3-(dipropylamino)methyl-4-hydroxyphenyl]-5-hydroxy-1-oxoisoquinoline

HRID 31108Notes

Reaction equation

HRID 31108 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[OH:27])[C:20](=[O:28])[NH:19][CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15]C)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].B(Br)(Br)Br.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[OH:27])[C:20](=[O:28])[NH:19][CH:18]=2)[CH:12]=[CH:13][C:14]=1[OH:15])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 22277759Boron tribromide dichloromethaneHCID 23077396HCID 23077396, compound

Product 1

HCID 230774171,2-Dihydro-4-[3-(dipropylamino)methyl-4-hydroxyphenyl]-5-hydroxy-1-oxoisoquinolineYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 63 (84.6 mg, 222 μmol) in dichloromethane (5 mL) was added 1 mol/L boron tribromide-dichloromethane solution (1.11 mL, 1.11 mmol), and the mixture was refluxed for 24 hours. After cooling, the reaction mixture was poured in ice water and the solution was brought to pH 8 with sodium carbonate. This was extracted using dichloromethane, dried over anhydrous sodium sulfate, and then solvent was distilled off. The residue obtained was purified by Chromatolex NH column chromatography [ethyl acetate-methanol=20:1], thereby affording 69.8 mg of the title compound as colorless powder. Yield 86%.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. extractionThis was extracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationsolvent was distilled off
  6. customThe residue obtained
  7. customwas purified by Chromatolex NH column chromatography [ethyl acetate-methanol=20:1]

Sources & evidence

ORD record
ord-72284069e66d4ad5887f371735d5e24f
Source dataset
uspto-grants-2008_09
Patent number
US07425563B2

Reaction notes

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