Methoxyisopropylamine → [4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine

HRID 1831526Notes

Reaction equation

HRID 1831526 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].[CH3:27][O:28][CH2:29][CH:30]([NH2:32])[CH3:31]>>[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:32][CH:30]([CH3:31])[CH2:29][O:28][CH3:27])[C:11]=1[N+:24]([O-:26])=[O:25]

Participants

3

Reactant 2

HCID 123458MethoxyisopropylamineHCID 86591985Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 22052173[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amineYield 68.6%

Procedure

Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester (0.48 g, 1.16 mmol), prepared substantially as described in Part C of Example 19a, and 2-methoxy-1-methyl-ethylamine (0.21 g, 2.32 mmol) were treated substantially as described in Part C of Example 19a to produce 0.28 g (68%) of [4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(2-methoxy-1-methyl-ethyl)-amine: MS (AP) m/z 351.8 [(M+H)+, 90].

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-4b4b2d213aff402aa4de8413991afd29
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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