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Dimethylformamide → 6-bromo-3-hydroxymethyl-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-one

HRID 750266
Notes
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Reaction equation

HRID 750266 reaction equation
CN(C=O)C.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:11]([C:29](O)=[O:30])=[C:10]2[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(Cl)(=O)C(Cl)=O>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=1)[C:11]([CH2:29][OH:30])=[C:10]2[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 230609586-Bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Product 1

HCID 230608406-bromo-3-hydroxymethyl-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

DMF (0.1 ml) was added to a suspension of 6-bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (5.5 g) in THF (55 ml), and oxalyl chloride (1.9 ml) was added dropwise under ice-cooling. The reaction mixture was allowed to warm to room temperature, stirred for 30 min., and concentrated under reduced pressure. The residue was suspended in a mixture of THF (90 ml) and 1,2-dimethoxyethane (90 ml), and under ice-cooling sodium borohydride (1.62 g) and methanol (3 ml) were added. The mixture was allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was poured into water under ice-cooling. 10% Hydrochloric acid was added to acidify the aqueous layer, and THF and methanol were evaporated under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diisopropyl ether to give the title compound (5.3 g).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was suspended in a mixture of THF (90 ml) and 1,2-dimethoxyethane (90 ml)
  5. temperatureunder ice-cooling sodium borohydride (1.62 g) and methanol (3 ml)
  6. additionwere added
  7. temperatureto warm to room temperature
  8. stirringstirred for 1 hr
  9. additionThe reaction mixture was poured into water under ice-
  10. temperaturecooling
  11. addition10% Hydrochloric acid was added
  12. customwere evaporated under reduced pressure
  13. extractionThe residue was extracted with ethyl acetate
  14. washthe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was evaporated under reduced pressure
  17. customthe obtained residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ce2cac6bf09e437087fe3aaaf2c9ded5
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes