Benzyl Bromide → HCID 54389750, compound

HRID 1195748Notes

Reaction equation

HRID 1195748 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH:5]2[C:15]([OH:17])=[O:16].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH:5]2[C:15]([O:17][CH2:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=1)=[O:16]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15157744HCID 15157744, compound

Product 1

HCID 54389750HCID 54389750, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-1,2,3,4-tetrahydroquinoline-4,8-dicarboxylic acid (10.2 g), benzyl bromide (9 ml) and potassium carbonate (10 g) in DMF (30 ml) was stirred at room temperature for 3 hours and filtered. To the filtrate was added a mixture of ethyl acetate-benzene (1:1, 300 ml). The mixture was washed with water, dried over anhydrous sodium sulfate and concentrated to give oily objective compound (17.44 g).

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added
  3. additiona mixture of ethyl acetate-benzene (1:1, 300 ml)
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b2468bef513d48e891c2a9f1d5e429c8
Source dataset
uspto-grants-1992_05
Patent number
US05112836

Reaction notes

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