Methanol → Methyl 6-amino-5-nitropyridine-3-carboxylate

HRID 427497Notes

Reaction equation

HRID 427497 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[OH-:14].[NH4+:15].[CH3:16]O>>[NH2:15][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:14][CH3:16])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 113680196-Chloro-5-nitronicotinoyl chloride

Product 1

HCID 13768248Methyl 6-amino-5-nitropyridine-3-carboxylateYield 45.9%

Procedure

6-Chloro-5-nitronicotinoyl chloride (22.0 g, 0.1 mol) was cooled to +5° C. Methanol was added dropwise during 30 min and the reaction mixture was stirred for 60 min. The temperature was not allowed to raise over +10° C. Ammonium hydroxide (25%, 400 ml) was added dropwise to the reaction mixture and the mixture was stirred at room temperature for 20 h. The product was filtered off, washed with water and dried to give 9.0 g (45.9%) of the title compound.

Workup

  1. temperatureto raise over +10° C
  2. stirringthe mixture was stirred at room temperature for 20 h
  3. filtrationThe product was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b8961e0ca40d41a384984305b55b3e15
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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