Dimethylformamide → HCID 14988481, compound

HRID 1885874Notes

Reaction equation

HRID 1885874 reaction equation
Br[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][CH2:5]2.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][N:30](C=O)C>>[C:29]([C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2)#[N:30]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14988463HCID 14988463, compound

Product 1

HCID 14988481HCID 14988481, compound

Procedure

To a solution of 6-bromo-1,2,3,4-tetrahydroquinoline-8-carboxylic acid (4.91 g) in DMF (80 ml) was added benzyl bromide (2.5 ml) and potassium carbonate (7.88 g). The reaction mixture was stirred at room temperature for an hour, and then insoluble material was filtered off. To this filtrate was added ethyl acetate-n-hexane (1:1, 400 ml), washed with water, aqueous saturated sodium chloride solution successively and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (6.71 g, quant.).

Workup

  1. filtrationinsoluble material was filtered off
  2. additionTo this filtrate was added ethyl acetate-n-hexane (1:1, 400 ml)
  3. washwashed with water, aqueous saturated sodium chloride solution successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bee7a33061074a2fa06c2ae407237676
Source dataset
uspto-grants-1992_09
Patent number
US05147874

Reaction notes

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