Ethyl Acetate → HCID 69428650, compound

HRID 1352491Notes

Reaction equation

HRID 1352491 reaction equation
C[O:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]([N:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:20](=[O:22])[CH3:21])[CH2:11][CH:10]2[CH3:29])=[O:8])=[CH:5][CH:4]=1.B(Br)(Br)Br.C(OCC)(=O)C>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([N:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:20](=[O:22])[CH3:21])[CH2:11][C@@H:10]2[CH3:29])=[O:8])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 3135989HCID 3135989, compound

Product 1

HCID 69428650HCID 69428650, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution N-[1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]-N-phenyl-acetamide (0.1 g) in dichloromethane (2.4 ml) at 0° C., was added boron tribromide (0.265 mmol). After 3 hours, ice and ethyl acetate were added and the solution was washed using water and carbonate potassium. The organic layer was separated and dried over sodium sulfate. The solvent was removed to afford an amorphous materiel. The product was purified by chromatography on silica gel using a mixture of dichloromethane and ethanol (95:5) as eluent to give the title compound (50 mg).

Workup

  1. washthe solution was washed
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. customto afford an amorphous materiel
  6. customThe product was purified by chromatography on silica gel using
  7. additiona mixture of dichloromethane and ethanol (95:5) as eluent

Sources & evidence

ORD record
ord-60ae02fdda684e4680e6623c27cf96d3
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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