Morpholine → 9-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 1583623Notes

Reaction equation

HRID 1583623 reaction equation
F[C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[Cl:20].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C)P(=O)(N(C)C)N(C)C>[O:24]1[CH2:25][CH2:26][N:21]([C:2]2[CH:14]=[C:12]3[C:13]4[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]3=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=4[C:3]=2[Cl:20])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 134729989-fluoro-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Product 1

HCID 130443029-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidYield 20.9%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

An autoclave containing a mixture of 3 g of 9-fluoro-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 8 g of morpholine and 30 ml of hexamethylphosphoric triamide was immersed in an oil bath at 190° C. and reaction was continued for 5 hours. After completion of reaction, the reaction mixture was cooled to precipitate crystals which then were collected by filtration. The crystals thus obtained were recrystallized from dimethylformamide to give 0.77 g of 9-morpholino-8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 271° to 274° C., white rhombic crystals.

Workup

  1. additionAn autoclave containing
  2. customwas immersed in an oil bath at 190° C.
  3. customreaction
  4. customAfter completion of reaction
  5. temperaturethe reaction mixture was cooled
  6. customto precipitate crystals which
  7. filtrationthen were collected by filtration
  8. customThe crystals thus obtained
  9. customwere recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-67aa6c012d6540fa82cea576215366c9
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

Loading…