Ammonia → HCID 478682, compound

HRID 54422Notes

Reaction equation

HRID 54422 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:28]=[CH:27][C:10]([C:11]([C:13](=[CH:19][NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:14](OCC)=[O:15])=[O:12])=[C:9](F)[CH:8]=2)=[CH:3][CH:2]=1.[H-].[Na+].[NH3:32]>O1CCOCC1>[C:21]1([N:20]2[C:27]3[C:10](=[CH:9][CH:8]=[C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH:28]=3)[C:11](=[O:12])[C:13]([C:14]([NH2:32])=[O:15])=[CH:19]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 178471913HCID 178471913, compound2×

Product 1

HCID 478682HCID 478682, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Novel quinolones (see Examples 1, 2, 3, 4, 5, 6 and 7) of this invention may be prepared by a mild ring closure reaction of ethyl 2-[4-(4-pyridyl)-2-fluoro-benzoyl]-3-phenylamino-propenoate (Formula 3) with sodium hydride in dioxane followed by treatment of the propeonate with ammonia to afford the desired 1,4-dihydro-1-phenyl-7-(4-pyridyl)-4-oxo-3-quinolinecarboxamide (Formula 5) as shown in Scheme 1.

Sources & evidence

ORD record
ord-42bbb3e9ac884247b6ea81709a723356
Source dataset
uspto-grants-1997_04
Patent number
US05622967

Reaction notes

Loading…