Dimethylformamide → HCID 178422953, compound

HRID 267505Notes

Reaction equation

HRID 267505 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12](O)=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)[CH:24]=[O:25]>>[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([CH2:12][C:24]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:25])=[CH:8][NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 53736724-Hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178422953HCID 178422953, compound

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-d798cd99aa324fcf9bd1f12ba2b3a220
Source dataset
uspto-grants-1976_03
Patent number
US03943141

Reaction notes

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