Hydrochloric Acid → 2-(3-chlorobenzyl)-9-hydroxy-7-phenyl-2H-pyrido[1,2-a]pyrazine-1,8-dione hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:30][CH:31](OC)OC)[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13](=[O:23])[C:14]=1[O:15]CC1C=CC=CC=1)=[O:8].Cl>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][N:6]1[CH:31]=[CH:30][N:10]2[CH:11]=[C:12]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:13](=[O:23])[C:14]([OH:15])=[C:9]2[C:7]1=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
3-Benzyloxy-1-(2,2-dimethoxyethyl)-4-oxo-5-phenyl-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (52 mg) was dissolved in acetic acid (0.5 ml) and conc. hydrochloric acid (0.5 ml) was added, and the mixture was stirred at 90° C. for 2 hr. The reaction mixture was concentrated, toluene was added to the residue and the mixture was concentrated, which operations were performed twice. Methanol was further added and the mixture was concentrated and crystallized from ethyl acetate-diisopropyl ether to give 2-(3-chlorobenzyl)-9-hydroxy-7-phenyl-2H-pyrido[1,2-a]pyrazine-1,8-dione hydrochloride (39 mg).
Workup
- concentrationThe reaction mixture was concentrated
- additiontoluene was added to the residue
- concentrationthe mixture was concentrated
- additionMethanol was further added
- concentrationthe mixture was concentrated
- customcrystallized from ethyl acetate-diisopropyl ether
Sources & evidence
- ORD record
- ord-d4cbc04d18734d5d81fbcb2ad98194d6
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211572B2
Reaction notes
Loading…