Sodium Hydroxide → HCID 9899727, compound

HRID 432669Notes

Reaction equation

HRID 432669 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[CH2:10][C:11]1[NH:12][C:13](=[O:21])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.[OH-].[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[CH2:10][C:11]1[NH:12][C:13](=[O:21])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 9899998HCID 9899998, compound

Product 1

HCID 9899727HCID 9899727, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1M; 8.5 ml, 8.5 mmol) was added dropwise under nitrogen to an ice-cooled, stirred suspension of 3-(3-methoxybenzyl) isoquinolinone (1 g, 3.8 mmol) in dichloromethane (5 ml), the stirred mixture was heated under reflux for 6 hours, then it was cooled to ambient temperature and poured onto 10% aqueous sodium hydroxide solution (30 ml). The basic solution was washed with dichloromethane (3×50 ml), then it was acidified by the addition of concentrated hydrochloric acid. The product was extracted into ethyl acetate (3×50 ml), the combined extracts were dried (MgSO4) and the solvent was removed in vacuo to leave 3-(3-hydroxybenzyl)isoquinolinone (0.4 g, 42%) as a white solid; m.pt. 225-227° C.; δH 3.80 (2H, s), 6.35 (1H, s), 6.60-7.70 (7H, m), 8.10 (1H, d), 9.30 (1H, s), 11.20 (1H, br s); m/z (M+H)+. 252 (100% purity).

Workup

  1. temperaturecooled
  2. temperaturethe stirred mixture was heated
  3. temperatureunder reflux for 6 hours
  4. washThe basic solution was washed with dichloromethane (3×50 ml)
  5. additionit was acidified by the addition of concentrated hydrochloric acid
  6. extractionThe product was extracted into ethyl acetate (3×50 ml)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-da9aa2007c5b40e28b54e5b09703ab8c
Source dataset
uspto-grants-2003_12
Patent number
US06664269B2

Reaction notes

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