3-Chloroquinoxaline-2-carboxylic acid → HCID 178522730, compound

HRID 1973359Notes

Reaction equation

HRID 1973359 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([OH:14])=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:15][C:16]1[NH:20][N:19]=[N:18][N:17]=1>O1CCCC1.CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]([NH:15][C:16]2[NH:20][N:19]=[N:18][N:17]=2)=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 139844723-Chloroquinoxaline-2-carboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522730HCID 178522730, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-2-quinoxalinecarboxylic acid (1.5 g) and N,N'-carbonyldiimidazole (1.2 g) in tetrahydrofuran (50 ml) were heated under reflux for 15 minutes. 5-Amino-1H-tetrazole (0.7 g) in dimethylformamide (5 ml) was added and the solution heated under reflux for 1 hour. The solvent was distilled off and the residue was triturated with dilute hydrochloric acid (25 ml., 2N). The solid was collected and crystallised from aqueous dimethylformamide. It had m.p. 257°-260° (d) (38%).

Workup

  1. temperatureunder reflux for 15 minutes
  2. temperaturethe solution heated
  3. temperatureunder reflux for 1 hour
  4. distillationThe solvent was distilled off
  5. customthe residue was triturated with dilute hydrochloric acid (25 ml., 2N)
  6. customThe solid was collected
  7. customcrystallised from aqueous dimethylformamide

Sources & evidence

ORD record
ord-55ddcfd7e52d4fc7a8342300fd3243c7
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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