Nalidixic Acid → HCID 178462612, compound

HRID 267504Notes

Reaction equation

HRID 267504 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[N:11]=2)[C:6](=[O:14])[C:5]([C:15]([OH:17])=O)=[CH:4]1)[CH3:2].[NH2:18][C:19]1[NH:23][N:22]=[N:21][N:20]=1>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[N:11]=2)[C:6](=[O:14])[C:5]([C:15]([NH:18][C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[O:17])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4421Nalidixic AcidHCID 178509299HCID 178509299, compound

Product 1

HCID 178462612HCID 178462612, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (4.1g) and N,N'-carbonyldiimidazole (2.85g) in dimethylformamide (30 ml) were stirred and heated at 100° for 3 hours and cooled. 5-Amino-1H-tetrazole (3.6 g) was added and the mixture was stirred at room temperature for 16 hours. The solid was collected and dissolved in aqueous dimethylaminoethanol and the solution was acidified to pH2 with dilute hydrochloric acid. The solid was filtered off and dried, m.p. above 289° (d), (60%)

Workup

  1. temperatureheated at 100° for 3 hours
  2. temperaturecooled
  3. customThe solid was collected
  4. dissolutiondissolved in aqueous dimethylaminoethanol
  5. filtrationThe solid was filtered off
  6. customdried

Sources & evidence

ORD record
ord-66b432184a8b4202b702e1b137b0e6dd
Source dataset
uspto-grants-1976_03
Patent number
US03943141

Reaction notes

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