Dimethylformamide → HCID 20028482, compound

HRID 1722251Notes

Reaction equation

HRID 1722251 reaction equation
IC.[CH2:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([OH:20])=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)[CH3:4].[C:21](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:3]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:20])[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:12]2[CH3:21])=[CH:7][CH:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469530HCID 178469530, compound

Product 1

HCID 20028482HCID 20028482, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodomethane (7.7 g) was added dropwise to a stirred mixture of ethyl 7-ethyl-4-hydroxyquinoline-3-carboxylate (12.1 g), anhydrous potassium carbonate (6.8 g) and dimethylformamide (125 ml) at ambient temperature. Stirring was continued for 30 hours. The solution was cooled in ice, diluted with 2 volumes of water and extracted with dichloromethane (3×100 ml). The extracts were combined, washed with water, dried over anhydrous sodium sulphate and evaporated. The residual oil was triturated with cold ethyl acetate. The resulting solid was collected, washed with ethyl acetate and recrystallised from ethyl acetate to give the novel compound ethyl 7-ethyl-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, m.p. 92°-94°.

Workup

  1. temperatureThe solution was cooled in ice
  2. extractionextracted with dichloromethane (3×100 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customThe residual oil was triturated with cold ethyl acetate
  7. customThe resulting solid was collected
  8. washwashed with ethyl acetate
  9. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9d00c824b1de436d9f0f2bc947a10457
Source dataset
uspto-grants-1989_08
Patent number
US04855291

Reaction notes

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