Dimethylformamide → HCID 14988481, compound

HRID 1031923Notes

Reaction equation

HRID 1031923 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-737b0bec09ab49f29ea9a8c67a77b94a
Source dataset
uspto-grants-1990_09
Patent number
US04956372

Reaction notes

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