Hydrochloric Acid → HCID 178418511, compound

HRID 3875Notes

Reaction equation

HRID 3875 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](N)[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]2[C:17](=[O:18])[NH:16][NH:15][CH:14]=[C:13]2[N:19]=1.N([O-])=O.[Na+].[ClH:24]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([Cl:24])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]2[C:17](=[O:18])[NH:16][NH:15][CH:14]=[C:13]2[N:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178418503HCID 178418503, compound

Product 1

HCID 178418511HCID 178418511, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An amount of 1.05 gm of 2-(2-methoxy-4-amino-phenyl)-5H-imidazo[4,5-d]pyridazin-4-one is suspended in 20 ml of 6N hydrochloric acid. The suspension is cooled to 0° to -3° C., and 0.28 gm of sodium nitrite, dissolved in 2 ml of water, are added dropwise thereto. The mixture is stirred for a further 40 minutes and then heated to 80°-85° C. for one hour. The product precipitated on cooling is purified by chromatography on silica gel [eluant: first methylene chloride/ethanol (100:0 to 100:20, then 1.5 to 2.5% of glacial acetic aicd is added)].

Workup

  1. temperatureThe suspension is cooled to 0° to -3° C.
  2. additionare added dropwise
  3. temperatureheated to 80°-85° C. for one hour
  4. customThe product precipitated
  5. temperatureon cooling
  6. customis purified by chromatography on silica gel [eluant
  7. additionfirst methylene chloride/ethanol (100:0 to 100:20, then 1.5 to 2.5% of glacial acetic aicd is added)]

Sources & evidence

ORD record
ord-8c990ec368674a9a9a4163d3dd8c972f
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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