Hydrochloric Acid → 10-(5-aminomethyl-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido [1,2,3-de][1,4]-benzoxazine-6-carboxylic acid
Reaction equation
C([NH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:15]1[C:16]([F:33])=[CH:17][C:18]3[C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:20]4[CH:21]([CH3:25])[CH2:22][O:23][C:24]=1[C:19]=34)[CH2:9]2)(=O)C.Cl.O.O1C2C=CC(C(O)=O)=CC=2C=CN1>C(O)C>[NH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:15]1[C:16]([F:33])=[CH:17][C:18]3[C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:20]4[CH:21]([CH3:25])[CH2:22][O:23][C:24]=1[C:19]=34)[CH2:9]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
315 mg of 10-(5-acetamidomethyl-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6carboxylic acid was added to a mixed solution of 12 ml of concentrated HCl, 2.5 ml of water, and 5 ml of ethanol, and the mixture was heated under reflux for 15 hours. After the mixture was concentrated under reduced pressure, the residue was recrystallized from ethanol to obtain 170 mg of 10-(5-aminomethyl-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]1,4]-benzoxazine-6-carboxylic acid.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 15 hours
- concentrationAfter the mixture was concentrated under reduced pressure
- customthe residue was recrystallized from ethanol
- customto obtain 170 mg of 10-(5-aminomethyl-2-isoindolinyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-
Sources & evidence
- ORD record
- ord-cda002c69e774e60bcf6526a3b4298ac
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05026856
Reaction notes
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