Potassium Hydroxide → HCID 19423741, compound

HRID 743644Notes

Reaction equation

HRID 743644 reaction equation
C([NH:4][CH:5]1[CH2:8][N:7]([C:9]2[C:10]([F:33])=[CH:11][C:12]3[C:13]([CH:32]=2)=[N:14][C:15]2[N:16]([N:28](C=O)[CH3:29])[CH:17]=[C:18]([C:23]([O:25]CC)=[O:24])[C:19](=[O:22])[C:20]=2[CH:21]=3)[CH2:6]1)(=O)C.[OH-].[K+]>>[NH2:4][CH:5]1[CH2:8][N:7]([C:9]2[C:10]([F:33])=[CH:11][C:12]3[C:13]([CH:32]=2)=[N:14][C:15]2[N:16]([NH:28][CH3:29])[CH:17]=[C:18]([C:23]([OH:25])=[O:24])[C:19](=[O:22])[C:20]=2[CH:21]=3)[CH2:6]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 19423646HCID 19423646, compound

Product 1

HCID 19423741HCID 19423741, compoundYield 74.3%

Conditions

Temperature
100 °C

Procedure

A suspension of 1.8 g of 8-(3-acetylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-(N-formyl-N-methylamino)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine in 40 cm3 of N aqueous potassium hydroxide is heated with stirring to a temperature in the region of 100° C. for 24 hours. After cooling to approximately 70° C., some slight insoluble matter is removed by filtration. At the same temperature, 40 cm3 of N methanesulphonic acid are added to the filtrate, and the precipitate formed is drained and washed with 3 times 20 cm3 of water at approximately 70° C. After recrystallization in 100 cm3 of dimethylformamide, 1.05 g of 8-(3-amino-1-azetidinyl)-7-fluoro-1-methylamino-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 315°-318° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to approximately 70° C.
  3. customsome slight insoluble matter is removed by filtration
  4. additionAt the same temperature, 40 cm3 of N methanesulphonic acid are added to the filtrate
  5. customthe precipitate formed
  6. washwashed with 3 times 20 cm3 of water at approximately 70° C
  7. customAfter recrystallization in 100 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-8a7e95fd4dcf4d90be49293f0fff3aa7
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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