Methylamine → HCID 29888498, compound

HRID 2244351Notes

Reaction equation

HRID 2244351 reaction equation
Cl[C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][NH2:13]>O1CCOCC1>[Cl:11][C:8]1[CH:9]=[N:10][C:2]([NH:13][CH3:12])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27360852,5-Dichloropyridine-3-carboxylic acid

Product 1

HCID 29888498HCID 29888498, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2,5-dichloronicotinic acid (1.76 g, 9.17 mmol), 41% aq. methylamine solution (7 mL), and 1,4-dioxane (6 mL) was heated at 160° C. under microwave irradiation for 20 min. After cooling, volatile material was distilled off, and the residue was dissolved in water (30 mL) and acidified to pH 3 by addition of 37% aq. hydrochloric acid solution. The precipitate was collected by filtration and triturated in DCM to produce the title compound (1.60 g, 92%). Off-white solid, MS (ISP): 187.1 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. distillationvolatile material was distilled off
  3. dissolutionthe residue was dissolved in water (30 mL)
  4. additionacidified to pH 3 by addition of 37% aq. hydrochloric acid solution
  5. filtrationThe precipitate was collected by filtration
  6. customtriturated in DCM

Sources & evidence

ORD record
ord-4acd24e1d6bc4973a8e19c5771fed078
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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