2-Chloro-5-methyl-3-nitropyridine → Ethyl 5-((5-methyl-3-nitropyridin-2-yl)amino)picolinate

HRID 588363Notes

Reaction equation

HRID 588363 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1.Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([CH3:23])=[CH:16][N:15]=1>>[CH3:23][C:17]1[CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=2)=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 8183002-Chloro-5-methyl-3-nitropyridineHCID 13816714Ethyl 5-aminopyridine-2-carboxylate

Product 1

HCID 117652979Ethyl 5-((5-methyl-3-nitropyridin-2-yl)amino)picolinateYield 53.4%

Procedure

Prepared according to General Procedure E starting from ethyl 5-aminopicolinate (14.0 g, 84.2 mmol) and 2-chloro-5-methyl-3-nitropyridine (17.4 g, 101 mmol) to give the title compound as a yellow solid (13.6 g, 53%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7e02379a946e45df80e56da4b1c97645
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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