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

HRID 1384157Notes

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

Participants

Conditions

Temperature: 30 °C

Procedure

The compound is prepared starting from 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.129 g meta-methylaniline in the manner described in Example 82A. After heating for 20 h to 130° C., siginificant quantities of 3-chloro-4,5-dimethyl-6 (pyridin-4-yl)methylpyridazine are still present (TLC). For this reason, a further 0.129 g meta-methylaniline is added and heated for another 24 h to 1 30° C. Processing is in the manner described for Example 82A. Title compound of about 90% purity is obtained after FC in CH2Cl2/methanol 19/1; m.p. 68-90%°. 1H-NMR (250 MHz, CDCl3): δ=8.45 (d, 2H); 7.70 (t, 1H); 7.50 (s, 1H); 7.40-7.10 (m, 4H)); 6.90 (d, 1H); 6.15 (s, wide, 1H); 4.30 (s, 2H); 2.35 (s, 3H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 305 (M+H).

Workup

customThe compound is prepared

Sources & evidence

ORD record: ord-70e38ad6cf664a948985e1e7ef0c8a14
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258812B1

Reaction notes

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