4-Heptanamine → [4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-propyl-butyl)-amine

HRID 1831515Notes

Reaction equation

HRID 1831515 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:11]=1[N+:24]([O-:26])=[O:25].[CH2:27]([CH:30]([NH2:34])[CH2:31][CH2:32][CH3:33])[CH2:28][CH3:29]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:34][CH:30]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][CH3:29])[C:11]=1[N+:24]([O-:26])=[O:25]

Participants

3

Reactant 2

HCID 386654-HeptanamineHCID 86591985Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 22052147[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-propyl-butyl)-amineYield 69%

Procedure

Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester(0.50 g, 1.21 mmol), prepared substantially as described in Part C of Example 19a, and 1-propyl-butylamine (0.28 g, 2.42 mmol) were treated in the same manner as in Part C of Example 19a to produce 0.31 g (69%) of [4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-propyl-butyl)-amine: MS (AP) m/z 377.9 [(M+H)+, 100].

Workup

  1. additionwere treated in the same manner as in Part C of Example 19a

Sources & evidence

ORD record
ord-eeb3e0c65b9746e1bd8ff83a29be0483
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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