7-Chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → HCID 178522725, compound

HRID 2398249Notes

Reaction equation

HRID 2398249 reaction equation
[Cl: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>[Cl: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 134959547-Chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522725HCID 178522725, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, (1 g) and N,N'-carbonyldiimidazole (1.1g) in dimethylformamide (12 ml) were heated at 100° for 1 hour. 5-Amino-1H-tetrazole (0.95 g) was added and the mixture was heated at 100° for 1 hour and cooled. The solid was filtered off and stirred with aqueous hydrochloric acid (10 ml, 2N) and the solid was collected and dried, m.p. above 350°.

Workup

  1. temperaturethe mixture was heated at 100° for 1 hour
  2. temperaturecooled
  3. filtrationThe solid was filtered off
  4. customthe solid was collected
  5. customdried

Sources & evidence

ORD record
ord-d379d24a5ca2477b8912b96a190a8de7
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

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