Hydrochloric Acid → HCID 135745143, compound

HRID 2073768Notes

Reaction equation

HRID 2073768 reaction equation
[NH2:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH2:10])=[O:9].Cl.[N:20]([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[C:2]3[N:1]=[N:20][NH:10][C:8](=[O:9])[C:7]=3[CH:6]=[CH:5][N:4]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 19856016HCID 19856016, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135745143HCID 135745143, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

300 mg of 3-amino-2-(4-methoxyphenyl)-4-pyridinecarboxamide were stirred at 0° C. in 5 ml of glacial acetic acid and 1 ml of concentrated hydrochloric acid during the addition of 128 mg of sodium nitrite in 2 ml of water. The cooling bath was removed, 3 ml of water were added, the mixture was stirred for 0.5 hour and the precipitated product was removed by filtration. Recrystallization from aqueous dimethylformamide yielded 275 mg of 8-(4-methoxyphenyl)pyrido[3,4-d]-1,2,3-triazin-4(3H)-one as yellow needles of melting point 226° C. (dec.).

Workup

  1. customThe cooling bath was removed
  2. addition3 ml of water were added
  3. customthe precipitated product was removed by filtration
  4. customRecrystallization from aqueous dimethylformamide

Sources & evidence

ORD record
ord-11b74dd978654fcab971564fd6ddd300
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

Loading…