Dimethylamine → HCID 12944900, compound

HRID 1578264Notes

Reaction equation

HRID 1578264 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1Cl)[N:11]([CH2:16][CH3:17])[CH:10]=[C:9]([C:18]([OH:20])=[O:19])[C:8]2=[O:21]>CN(C=O)C.COCCO>[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[N:2]([CH3:3])[CH3:1])[N:11]([CH2:16][CH3:17])[CH:10]=[C:9]([C:18]([OH:20])=[O:19])[C:8]2=[O:21]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 12733886HCID 12733886, compound

Product 1

HCID 12944900HCID 12944900, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80192-MethoxyethanolSolvent

Procedure

13 g of dimethylamine were dissolved in a mixture of DMF (20 cm3) and methyl cellosolve (20 cm3). 4.3 g of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid were added and the mixture was heated, whilst stirring, in an autoclave at 120°-130° C. for 7 hours. After cooling, the solution was concentrated to dryness in vacuo and the residue was taken up in 20 cm3 of water. The solid was filtered off and recrystallised from methyl cellosolve (30 cm3). 3.9 g of 6-chloro-7-dimethylamino-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 210° C., were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated to dryness in vacuo
  4. filtrationThe solid was filtered off
  5. customrecrystallised from methyl cellosolve (30 cm3)

Sources & evidence

ORD record
ord-945c670d3ba04033bea5c58562322154
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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