P-Anisidine → 3-(4-Methoxyanilino)-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

HRID 49916Notes

Reaction equation

HRID 49916 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][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(Cl)Cl.CO>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][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:21][CH:20]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 107760253-Chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

Product 1

HCID 227420183-(4-Methoxyanilino)-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The compound is prepared from 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.129 g para-methoxyaniline in the manner described in Example 82A. Title compound is obtained after FC in CH2Cl2/Methanol 19/1. 1H-NMR (250 MHz, CDCl3): δ=8.45 (d, 2H); 7.45 (d, 2H); 7.10 (d, 2H); 6.85 (d, 2H); 6.05 (s, wide, 1H); 4.25 (s, 2H); 3.80 (s, 3H); 2.30 (s, 3H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 321 (M+H).

Sources & evidence

ORD record
ord-36d559b8627241f7a2a08c2160e1ef03
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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