Morpholine → HCID 1505698, compound

HRID 434571Notes

Reaction equation

HRID 434571 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 1505698HCID 1505698, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.43 g), morpholine (1.4 g), and pyridine (3 ml) was refluxed for 6 hours. After the mixture evaporated to dryness, the residue was acidified with aqueous acetic acid and extracted with dichloromethane. The organic layer was washed with water, dried, and evaporated. The solid was recrystallized from a mixture of DMF and ethanol and gave 1-ethyl-6,8-difluoro-1,4-dihydro-7-(4-morpholinyl)-4-oxoquinoline-3-carboxylic acid (0.28 g), mp 268°-271° C. (decomp.).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customAfter the mixture evaporated to dryness
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe solid was recrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-726b0e14d603450c95e0b35af1d3bcb4
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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