Morpholine → HCID 12944904, compound

HRID 1578268Notes

Reaction equation

HRID 1578268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]([CH3:13])[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:8]([CH3:13])[CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 54183884HCID 54183884, compound

Product 1

HCID 12944904HCID 12944904, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.18 g of 6,7-dichloro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 3 cm3 of morpholine and 30 cm3 of DMSO were heated for 5 hours at 125°-130° C. About 3 hours were required for total dissolution of the dihalogeno-acid, and the reaction product then precipitated from the mixture. After returning to room temperature, the mixture was diluted with 30 cm3 of water. The precipitate was filtered off, washed with water and recrystallised from a mixture of DMF (1 volume) and methylcellosolve (1 volume). 1.68 g of 6-chloro-1-methyl-7-morpholino-4-oxo-1,4-dihydro quinoline-3-carboxylic acid were obtained; m.p. 334° C.

Workup

  1. customthe reaction product then precipitated from the mixture
  2. customAfter returning to room temperature
  3. additionthe mixture was diluted with 30 cm3 of water
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customrecrystallised from a mixture of DMF (1 volume) and methylcellosolve (1 volume)

Sources & evidence

ORD record
ord-3c5b87e6dee04cdf8ab283d852c12217
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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