p-Toluidine → 3-(4-Methylanilino)-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

HRID 49915Notes

Reaction equation

HRID 49915 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>CO>[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[N:3]=[N:4][C:5]([CH2:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]([CH3:9])[C:7]=2[CH3:8])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 107760253-Chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

Product 1

HCID 227420193-(4-Methylanilino)-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound is prepared from 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.129 g para-methylaniline in the manner described in Example 82A. Title compound is obtained after FC in CH2Cl/Methanol 19/1; m.p. 68-70° C. 1H-NMR (250 MHz, CDCl3): δ=8.45 (s, wide, 2H); 7.45 (d, 2H); 7.10 (“d”, wide, 4H); 6.10 (s, wide, 1H); 4.25 (s, 2H); 2.30 (s, 3H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 305 (M+H).

Sources & evidence

ORD record
ord-490404542a264d5d989e2e57034ad032
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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