Hydrochloric Acid → HCID 15136244, compound

HRID 981279Notes

Reaction equation

HRID 981279 reaction equation
[CH:1]1([C:4]2[C:13](F)=[C:12]3[C:7]([C:8](=[O:24])[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][N:11]3[CH:15]([CH3:18])[CH2:16][OH:17])=[C:6]([F:25])[C:5]=2[F:26])[CH2:3][CH2:2]1.[H-].[Na+].C(OCC)(=O)C.Cl>CN(C)C=O.O>[CH:1]1([C:4]2[C:5]([F:26])=[C:6]([F:25])[C:7]3[C:8](=[O:24])[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][N:11]4[CH:15]([CH3:18])[CH2:16][O:17][C:13]=2[C:12]=34)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15136243HCID 15136243, compound

Product 1

HCID 15136244HCID 15136244, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 1.7 ml of N,N-dimethylformamide was dissolved 170 mg of ethyl 7-cyclopropyl-5,6,8-trifluoro-1-(2-hydroxy-1-methylethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate. To the resulting solution was added 20 mg of 60% sodium hydride. The resulting mixture was stirred at 80°-90° C. for 15 hours. The reaction mixture was added to a mixture of 5 ml of ethyl acetate and 5 ml of water. The resulting mixture was adjusted to pH 1.5 with 2N hydrochloric acid. The resulting crystals were collected by filtration to obtain 63 mg (yield: 39.1%) of ethyl 10-cyclopropyl-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate.

Workup

  1. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-5075048a0741476782eddd98e65eb1be
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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