Sodium → HCID 135745109, compound

HRID 2073765Notes

Reaction equation

HRID 2073765 reaction equation
[NH2:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([NH2:10])=[O:9].[N:21]([O-])=O.[Na+].[Na]>Cl.O.C(OCC)(=O)C>[F:19][C:17]([F:20])([F:18])[C:13]1[CH:12]=[C:11]([C:3]2[C:2]3[N:1]=[N:21][NH:10][C:8](=[O:9])[C:7]=3[CH:6]=[CH:5][N:4]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 5360545SodiumHCID 19855980HCID 19855980, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135745109HCID 135745109, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

562 mg of 3-amino-2-(3-trifluoromethylphenyl)-4-pyridinecarboxamide were stirred at 0° C. in 5 ml of concentrated hydrochloric acid during the addition of 160 mg of sodium nitrite in 1 ml of water. After 0.5 hour the mixture was diluted with water and ethyl acetate and made basic with sodium hicarbonate. The organic phase was separated, dried over sodium sulphate and evaporated, and the residue was purified by chromatography on silica gel using ethyl acetate/petroleum ether (1:1) for the elution. There were obtained 400 mg of 8-(3-trifluoromethylphenyl)pyrido[3,4-d]-1,2,3-triazin-4(3H)-one in the form of a solid of melting point 192°-193° C. (dec.).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customthe residue was purified by chromatography on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-5c2362f086ae482db021f02e9c9a1b57
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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