HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetic Acid → 1,8-naphthyridine-3-carboxylic Acid

HRID 1084391
Notes
Print preview

Reaction equation

HRID 1084391 reaction equation
FC1C(F)=C(F)[C:5]2=[N:6][C:7]3[N:8](C)[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=O)[C:12]=3[CH:13]=[C:4]2C=1.CN1CCNCC1.O.C(O)(=O)C>CS(C)=O>[N:8]1[C:7]2[C:12](=[CH:13][CH:4]=[CH:5][N:6]=2)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 531671-MethylpiperazineHCID 194236787,8,9-Trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 47383911,8-naphthyridine-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4 g of 7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid in 60 cm3 of dimethyl sulphoxide and 3 g of 1-methylpiperazine is heated at 80° C. for 1 hour and a half. After cooling to about 20° C., 150 cm3 of water are added. 18 cm3 of 10% acetic acid are added to the solution obtained. The precipitate formed is drained, washed with 3 times 50 cm3 of water and recrystallized from 50 cm3 of dimethylformamide. 4 g of 7,9-difluoro-1-methyl-8-(4-methyl-1-pip-erazinyl)-4-oxo-1,4-dihydrobenzo[b]1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 316° C..

Workup

  1. temperatureAfter cooling to about 20° C.
  2. customobtained
  3. customThe precipitate formed
  4. washwashed with 3 times 50 cm3 of water
  5. customrecrystallized from 50 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-1d9adb8e5949442181481b9b7b2da446
Source dataset
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05004745

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes