Water → HCID 21923119, compound

HRID 2222286Notes

Reaction equation

HRID 2222286 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.Br[CH:13]([CH2:18][CH3:19])[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH:13]([CH2:18][CH3:19])[C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 95577Butanoic acid, 2-bromo-, methyl ester

Product 1

HCID 21923119HCID 21923119, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Hydroxyquinoline (25.1 g), methyl 2-bromobutyrate (32.3 g) and anhydrous potassium carbonate (23.0 g) in dry N,N-dimethylformamide (100 ml) were stirred at 100° C. for 3 hours then stored at ambient temperature for 18 hours. The mixture was added to water, extracted with ethyl acetate (three times) and the extracts combined, washed with water (four times) then dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the required product (39.0 g) as a red oil.

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. washwashed with water (four times)
  3. dry with materialthen dried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f83c0515e94a417994d4bc52e0658d61
Source dataset
uspto-grants-2008_05
Patent number
US07371764B2

Reaction notes

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