Ammonia → Ethyl 4-amino-6-chloro-5-nitronicotinate

HRID 1268831Notes

Reaction equation

HRID 1268831 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4](C)[C:3]=1[C:13]([OH:15])=[O:14].[CH2:16](N(CC)CC)[CH3:17].[NH3:23].O1CCOCC1>ClCCl>[CH2:16]([O:15][C:13]([C:3]1[CH:4]=[N:5][C:6]([Cl:11])=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH2:23])=[O:14])[CH3:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 203278654,6-dichloro-2-methyl-5-nitro-3-Pyridinecarboxylic acid

Product 1

HCID 45588416Ethyl 4-amino-6-chloro-5-nitronicotinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,6-Dichloro-2-methyl-5-nitro-pyridine-3-carboxylic acid (15 g, 56.6 mmol) and triethylamine (7.9 mL, 57.3 mmol) in dichloromethane (84 mL) at 0° C. was added dropwise ammonia solution in dioxane (0.5 M, 113 mL, 56.5 mmol). The mixture was then stirred overnight. Removal of the solvent followed by column chromatography gave 9 as a yellow crystalline solid. (7.3 g). 1H-NMR δ: 1.32 (t, J=7.1 Hz, 3H), 4.33 (q, J=7.1 Hz, 2H), 8.06 (s, br, 2H), 8.62 (s, 1H).

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-a0d1c99674914fde8fc14542af2d2dbb
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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