Dimethylformamide → HCID 12769805, compound

HRID 894824Notes

Reaction equation

HRID 894824 reaction equation
[Na].[CH2:2]([O:4][C:5]([C:7]1[C:8](=[O:19])[NH:9][C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][C:13]([Cl:18])=[CH:12][CH:11]=2)=[O:6])[CH3:3].CN(C)C=O.[CH2:25](Br)[CH:26]=[CH2:27]>O>[CH2:2]([O:4][C:5]([C:7]1[C:8](=[O:19])[N:9]([CH2:27][CH:26]=[CH2:25])[C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][C:13]([Cl:18])=[CH:12][CH:11]=2)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 5360545SodiumHCID 12769804HCID 12769804, compound

Product 1

HCID 12769805HCID 12769805, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.66 g. (0.03 mole) of the sodium salt of 4-amino-6-chloro-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid ethyl ester in 50 ml. of dimethyl formamide was added 4.84 g. (0.04 mole) of allyl bromide. The reaction mixture was heated on a steam bath for 2 hours and was then cooled to room temperature. The reaction mixture was poured into 500 ml. of water. The reaction mixture was allowed to stand for several hours at room temperature and was then filtered. There was obtained 7.6 g. of product. Recrystallization from ethyl acetate gave 3.4 g. of product, m.p. 144°-146° C.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 2 hours
  2. additionThe reaction mixture was poured into 500 ml
  3. waitto stand for several hours at room temperature
  4. filtrationwas then filtered
  5. customThere was obtained 7.6 g
  6. customRecrystallization from ethyl acetate
  7. customgave 3.4 g

Sources & evidence

ORD record
ord-ccd64beae8204ee0b836720452977cf5
Source dataset
uspto-grants-1981_08
Patent number
US04284768

Reaction notes

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