3-Chloroaniline → HCID 22741983, compound

HRID 1057734Notes

Reaction equation

HRID 1057734 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].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C(Cl)Cl.CO>[Cl: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

4

Reactant 2

HCID 79323-Chloroaniline2×HCID 107760253-Chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine2×

Product 1

HCID 22741983HCID 22741983, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The compound is prepared starting from 0.070 g 3-chloro-4,5-dimethyl-6-(pyridin-4-yl)methylpyridazine and 0.153 g meta-chloroaniline 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 0.153 g meta-chloroaniline is added and heated for another 24 h to 130° C. Processing is in the manner described for Example 82A. Title compound is obtained after FC in CH2Cl2/methanol 19/1: m.p. 164-167°. 1H-NMR (250 MHz, CDCl3): δ=8.45 (s, wide, 2H); 7.70 (t, 1H); 7.45 (dd, 1H); 7.25-7.10 (m, 3H)); 7.00 (dd, 1H); 6.20 (s, wide, 1H); 4.25 (s, 2H); 2.15 (s, 3H); 2.10 (s, 3H). ES-MS 325, 327 (M+H for 35Cl and 37Cl).

Workup

  1. customThe compound is prepared
  2. temperatureheated for another 24 h to 130° C

Sources & evidence

ORD record
ord-18651e10f52a4b338ae444e16262dafe
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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