Dimethylformamide → 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Benzyl Ester

HRID 750131Notes

Reaction equation

HRID 750131 reaction equation
[CH2:1]([N:8]1[C:17]([C:18]([OH:20])=[O:19])=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:27])[CH:14]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CN(C=O)C>O>[CH2:35]([O:19][C:18]([C:17]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:28])[C:10]2[C:15]([C:16]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:14][C:13]([Br:27])=[CH:12][CH:11]=2)=[O:20])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 230606482-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 691560522-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Benzyl EsterYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (150 mg), potassium carbonate (95 mg), benzylbromide (81 μl) and DMF (5 ml) was stirred at room temperature for 3 hrs. After diluting with water, the mixture was extracted with ether. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and ethyl acetate and n-hexane was added to the residue. The mixture was crystallized to give the title compound (152 mg, 84%).

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure and ethyl acetate and n-hexane
  5. additionwas added to the residue
  6. customThe mixture was crystallized

Sources & evidence

ORD record
ord-a6b1e74b0e42467d9f156be68b85b5cf
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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