1-methoxymethyl-propylamine HCl → [4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine

HRID 1831511Notes

Reaction equation

HRID 1831511 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.[CH3:27][O:28][CH2:29][CH:30]([NH2:33])[CH2:31][CH3:32]>>[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]([NH:33][CH:30]([CH2:29][O:28][CH3:27])[CH2:31][CH3:32])[C:10]=1[N+:23]([O-:25])=[O:24]

Participants

3

Reactant 2

HCID 220520451-methoxymethyl-propylamine HClHCID 86591984Trifluoro-methanesulfonic acid 4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl-ester

Product 1

HCID 22052219[4-(2,4-Dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amineYield 79.3%

Procedure

Trifluoro-methanesulfonic acid 4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl-ester (3.0 g, 7.19 mmol), prepared substantially as described in Part C of Example 19a, and 1-methoxymethyl-propylamine HCl (2.01 g, 14.4 mmol) were treated substantially as described in Part C of Example 19a to produce 2.11 g (79%) of [4-(2,4-dichloro-phenyl)-3-nitro-pyridin-2-yl]-(1-methoxymethyl-propyl)-amine: MS (AP) m/z 370.2 [(M+H)+, 100].

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-a63b92cff834427d9361655d7d15a5f6
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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