HCID 13577655, compound → HCID 70454914, compound

HRID 2418241Notes

Reaction equation

HRID 2418241 reaction equation
[F:1][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[O:20]C>Br.O>[OH2:15].[F:1][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[OH:20]

Participants

4

Reactant 1

HCID 13577655HCID 13577655, compound

Product 1

HCID 70454914HCID 70454914, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 1.2 g of 6,7-dihydro-9-fluoro-8-methoxy-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in 25 ml of 48% hydrobromic acid was heated at reflux for three hours, and was then cooled and diluted with about 100 ml of water. The product was separated by filtration and recrystallized from aqueous N,N-dimethylformamide to provide white solid 6,7-dihydro-9-fluoro-8-hydroxy-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrate, m.p. 293°-294° C. Analysis: Calculated for C14H12FNO4.0.25H2O=%C, 59.7; %H, 4.5; %N, 5.0; Found: %C, 59.5; %H, 4.2; %N, 5.0.

Workup

  1. temperatureat reflux for three hours
  2. temperaturewas then cooled
  3. customThe product was separated by filtration
  4. customrecrystallized from aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-f94323df4ce04ae795eac5b6ff55265f
Source dataset
uspto-grants-1984_09
Patent number
US04472407

Reaction notes

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