4-Hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid → HCID 178422964, compound

HRID 2398237

Reaction equation

HRID 2398237 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([OH:14])=O)=[CH:8][NH:9]2)=[CH:4][CH:3]=1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>CN(C)C=O>[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:14])=[CH:8][NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 53736724-Hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178422964HCID 178422964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (4 g) and N,N'-carbonyldiimidazole (3.5 g) in dimethylformamide (40 ml) were heated at 80° for 6 hours. 5-Amino-1H-tetrazole (2.5 g) was added and the mixture was stirred and heated at 80° for 1.5 hours. The solid was collected and dissolved in aqueous sodium hydroxide. The solution was acidified with glacial acetic acid and the solid was collected and dried. It had m.p. 344°-345.5°, (47%)

Workup

  1. temperatureheated at 80° for 1.5 hours
  2. customThe solid was collected
  3. dissolutiondissolved in aqueous sodium hydroxide
  4. customthe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-b4590d6fd806448088eb4623c006433b
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Linked notes

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