Dimethylformamide → HCID 12769799, compound

HRID 894820Notes

Reaction equation

HRID 894820 reaction equation
[Na].[CH2:2]([O:4][C:5]([C:7]1[C:8](=[O:18])[NH:9][C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:6])[CH3:3].CN(C)C=O.[CH2:24](Br)[CH:25]=[CH2:26]>O>[CH2:2]([O:4][C:5]([C:7]1[C:8](=[O:18])[N:9]([CH2:26][CH:25]=[CH2:24])[C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 5360545SodiumHCID 12769797Ethyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 12769799HCID 12769799, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing 7.6 g. (0.03 mole) of the sodium salt of 4-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid ethyl ester in 50 ml. of dimethylformamide was added 4.8 g. (0.04 mole) of allyl bromide. The reaction mixture was heated on a steam bath for 1/2 hour. The reaction mixture was cooled in ice and poured into 500 ml. of water. The resulting precipitate was collected on a filter and recrystallized from ethyl acetate-petroleum ether giving 4.6 g. of product, m.p. 132°-134° C.

Workup

  1. additionTo a solution containing 7.6 g
  2. temperatureThe reaction mixture was heated on a steam bath for 1/2 hour
  3. temperatureThe reaction mixture was cooled in ice
  4. additionpoured into 500 ml
  5. customThe resulting precipitate was collected on
  6. filtrationa filter
  7. customrecrystallized from ethyl acetate-petroleum ether giving 4.6 g

Sources & evidence

ORD record
ord-59d059f64176436fb38cbc8dbc53497f
Source dataset
uspto-grants-1981_08
Patent number
US04284768

Reaction notes

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