1-Cyclopropylbutan-1-amine hydrochloride → (1-Cyclopropyl-butyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine

HRID 1831502Notes

Reaction equation

HRID 1831502 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11](OS(C(F)(F)F)(=O)=O)[C:10]=1[N+:23]([O-:25])=[O:24].Cl.[CH:27]1([CH:30]([NH2:34])[CH2:31][CH2:32][CH3:33])[CH2:29][CH2:28]1>>[CH:27]1([CH:30]([NH:34][C:11]2[C:10]([N+:23]([O-:25])=[O:24])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH:14]=[CH:13][N:12]=2)[CH2:31][CH2:32][CH3:33])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 696580151-Cyclopropylbutan-1-amine hydrochlorideHCID 86591984Trifluoro-methanesulfonic acid 4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl-ester

Product 1

HCID 22052181(1-Cyclopropyl-butyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amineYield 72.3%

Procedure

Trifluoro-methanesulfonic acid 4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl-ester (1.0 g, 2.40 mmol), prepared substantially as described in Part C of Example 19a, and 1-cyclopropyl-butylamine HCl (1.0 g, 4.79 mmol) were treated substantially as described in Part C of Example 19a to produce 0.66 g (72%) of crude (1-cyclopropyl-butyl)-[4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-amine: MS (AP) m/z 380.3 [(M+H)+, 100].

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-f5a3e40aae9348d5874a4dda43f1a47b
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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