4-Chloroaniline → HCID 11222131, compound

HRID 1813971Notes

Reaction equation

HRID 1813971 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])[N:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([C:4]2[N:3]=[C:2]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=3)[CH:7]=[C:6]([NH2:8])[CH:5]=2)[CH:14]=1

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 22504957HCID 22504957, compound

Product 1

HCID 11222131HCID 11222131, compoundYield 22%

Procedure

Following the method described in Example 3, 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyridin-4-yl-amine and 4-chloro-phenylamine, provided the title compound (22% yield). 1H NMR (acetone-d6) δ 3.90 (s, 3H, CH3), 5.39 (s, 2H, NH2), 6.90 (d, 1H, J=1.7 Hz, Ar), 7.12 (d, 1H, J=8.8 Hz, Ar), 7.24 (d, 2H, J=8.9 Hz, Ar), 7.34 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.73 (d, 2H, J=8.9 Hz, Ar), 7.91 (d, 1H, J=2.8 Hz, Ar), 8.09 (s, 1H, NH).

Sources & evidence

ORD record
ord-0da58c54a58145948ffdb8d02a237f92
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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