3-Phenylpyridazine → HCID 20226917, compound

HRID 1731713Notes

Reaction equation

HRID 1731713 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N:5][C:6]([CH:10]2[CH2:15][CH2:14][CH:13](C)[CH2:12][CH2:11]2)=[CH:7][C:8]=1[CH3:9].C1(C2N=NC(OC)=C(C)C=2C)CCCCC1.C1(C2N=NC=CC=2)C=CC=CC=1>>[CH:10]1([C:6]2[N:5]=[N:4][C:3]([O:2][CH3:1])=[C:8]([CH3:9])[CH:7]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 1934993-PhenylpyridazineHCID 20226931HCID 20226931, compoundHCID 20226933HCID 20226933, compound

Product 1

HCID 20226917HCID 20226917, compound

Procedure

A mixture of 4-methyl-3-methoxy-6-phenylpyridazine (5.0 g), platinum dioxide (400 mg) and trifluoroacetic acid (20 mL) is shaken in a Parr apparatus until hydrogen uptake ceases. The catalyst is removed by filtration, and the cake is washed with additional acid. The filtrate is poured into water and adjusted to basic ph with sodium hydroxide. The solids which precipitate are collected, washed with water, and dried to give 4.6 g (90%) of product which, on crystallization from pentane, gives an analytically pure product having a melting point of 72°-74° C. 3-Methoxy-4-methyl-6-(4-methylcyclohexyl)pyridazine, melting point 84°-98° C. (Example 29a), and 3-cyclohexyl-6-methoxy-4,5-dimethylpyridazine, melting point 99°-101° C. (Example 29b) are also made by the above procedure using the corresponding 6-phenylpyridazine.

Workup

  1. customon crystallization from pentane
  2. customgives an analytically pure product

Sources & evidence

ORD record
ord-44da0cfb29154eb29e0392fce512dff0
Source dataset
uspto-grants-1986_11
Patent number
US04623376

Reaction notes

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