Ammonia → 3-Amino-6-(3-methoxy-4-propoxyphenyl)pyridazine

HRID 2399352Notes

Reaction equation

HRID 2399352 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:6][CH:7]=1.[NH3:20]>C(O)CO.O>[NH2:20][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 193854943-Chloro-6-(3-methoxy-4-propoxyphenyl)pyridazine

Product 1

HCID 98816183-Amino-6-(3-methoxy-4-propoxyphenyl)pyridazineYield 81.7%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

10 g (35.9 mmol) of 3-chloro-6-(3-methoxy-4-propoxyphenyl)pyridazine are heated in 50 ml of ethylene glycol which has been saturated with ammonia at 0° C. in an autoclave at 220° C. for 6 hours. After cooling, the reaction mixture is diluted with 500 ml of water, and the precipitate which forms is filtered off with suction. The crude product is dried and then purified by column chromatography on silica gel with chloroform as eluent. 7.6 g (81.7%) of the title compound of m.p. 147° C. are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate which forms is filtered off with suction
  3. dry with materialThe crude product is dried
  4. custompurified by column chromatography on silica gel with chloroform as eluent

Sources & evidence

ORD record
ord-84d88bd43b4e41769693a55c6b67f8c3
Source dataset
uspto-grants-1995_09
Patent number
US05449676

Reaction notes

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