Hydrochloric Acid → HCID 11197026, compound

HRID 344860Notes

Reaction equation

HRID 344860 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])C.Cl>C(O)(=O)C>[F:21][C:19]1[C:18]([F:22])=[CH:17][C:11]2=[N:12][C:13]3[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:23])[C:8]=3[CH:9]=[C:10]2[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 11197026HCID 11197026, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine (8 g) in 17.5% strength aqueous hydrochloric acid solution (80 cc) and acetic acid (80 cc) is heated with stirring to a temperature in the region of 100° C. for 1 hour and a half. After cooling to approximately 20° C., the solid is drained and washed with water (6×100 cc). After 1 recrystallization in dimethylformamide (160 cc), 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3 -carboxylic acid (6.44 g) is obtained in the form of a yellow solid, decomposing at 360° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to approximately 20° C.
  3. washwashed with water (6×100 cc)
  4. customAfter 1 recrystallization in dimethylformamide (160 cc)

Sources & evidence

ORD record
ord-056b6486e6cb46f1a0694823e676ed5b
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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