Ammonia → 1-Ethyl-1,4-dihydro-4-oxo-6-fluoro-7-amino-1,8-naphthyridine-3-carboxylic acid

HRID 1583551Notes

Reaction equation

HRID 1583551 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Cl)[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[NH3:19].C(O)C>C(O)(=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([NH2:19])[N:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 135060151-Ethyl-1,4-dihydro-4-oxo-6-fluoro-7-amino-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 Gram of 1-ethyl-1,4-dihydro-4-oxo-6-fluoro-7-chloro-1,8-naphthyridine-3-carboxylic acid (for example, described in European Patent Application No. 0,027,752) is mixed with 25 ml of concentrated ammonia solution containing 20% of ethanol. The mixture is maintained in a sealed tube for 4 hours at 120°-125° C. The mixture is cooled, and acetic acid added until the pH is slightly acid, when the precipitate formed is filtered off and washed with water. The product is dried, 0.8 gram of 1-ethyl-1,4-dihydro-4-oxo-6-fluoro-7-amino-1,8-naphthyridine-3-carboxylic acid being obtained, of melting point 299°-303° C.

Workup

  1. temperatureThe mixture is maintained in a sealed tube for 4 hours at 120°-125° C
  2. temperatureThe mixture is cooled
  3. customformed
  4. filtrationis filtered off
  5. washwashed with water
  6. customThe product is dried

Sources & evidence

ORD record
ord-09af9dd3fdd24d0eb9855e7a915af4e5
Source dataset
uspto-grants-1985_11
Patent number
US04552882

Reaction notes

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