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1-(2-Hydroxyethyl)piperazine → 1,8-naphthyridine-3-carboxylic Acid

HRID 1084360
Notes
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Reaction equation

HRID 1084360 reaction equation
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[OH:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][OH:22])[CH2:26][CH2:27]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1.[N:9]1[C:8]2[C:13](=[CH:14][CH:5]=[CH:6][N:7]=2)[CH:12]=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 2

HCID 47383911,8-naphthyridine-3-carboxylic AcidHCID 14700563HCID 14700563, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Fluoro-8-[4-(2-hydroxyethyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Example 1 but starting from 1.6 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 6.8 g of 1-(2-hydroxyethyl)piperazine in 16 cm3 of pyridine. After concentrating the reaction mixture to dryness under reduced pressure, the residue is taken up in 50 cm3 of water. The mixture is brought to pH 6.9 by adding 0.4 cm3 of acetic acid. The precipitate obtained is drained, washed with twice 10 cm3 of water and recrystallized twice from 10 cm3 of dimethyl-formamide. 1.1 g of 7-fluoro-8-[4-(2-hydroxyethyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydro-benzo[b]1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 275°-276° C.

Workup

  1. concentrationAfter concentrating the reaction mixture to dryness under reduced pressure
  2. additionby adding 0.4 cm3 of acetic acid
  3. customThe precipitate obtained
  4. washwashed with twice 10 cm3 of water
  5. customrecrystallized twice from 10 cm3 of dimethyl-formamide

Sources & evidence

ORD record
ord-bf80fdd02adb41e38e0dd390ec2bca2e
Source dataset
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05004745

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes