HCID 21435004, compound → HCID 178466021, compound

HRID 2398247Notes

Reaction equation

HRID 2398247 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:22])[C:9]([C:19]([OH:21])=O)=[CH:10][N:11]2[CH2:14][CH2:15][O:16]C=O)=[CH:6][CH:5]=1)[CH3:2].[NH2:23][C:24]1[NH:28][N:27]=[N:26][N:25]=1>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:22])[C:9]([C:19]([NH:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[O:21])=[CH:10][N:11]2[CH2:14][CH2:15][OH:16])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21435004HCID 21435004, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178466021HCID 178466021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Ethoxy-1(2-formyloxyethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (0.5 g) and N,N'-carbonyldiimidazole (0.4 g) in dimethylformamide (10 ml) were stirred and heated to 80° for 6 hours. 5-Amino-1H-tetrazole (0.42 g) was added and the mixture stirred and heated to 80° for 30 minutes. The solid was collected and dissolved in aqueous sodium hydroxide (10 ml, 2N) and the solution was acidified to pH 1 with dilute hydrochloric acid. The solid was filtered off, washed with water and dried, m.p. above 297° (d). (45%).

Workup

  1. temperatureheated to 80° for 6 hours
  2. temperatureheated to 80° for 30 minutes
  3. customThe solid was collected
  4. dissolutiondissolved in aqueous sodium hydroxide (10 ml, 2N)
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-151cdfd956824c26b763c12d5a72b281
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

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