Methylamine → 946119-30-8

HRID 2244352Notes

Reaction equation

HRID 2244352 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([C:9]([OH:11])=[O:10])[N:3]=1.[CH3:12][NH2:13]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=[O:10])[C:5]([NH:13][CH3:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 447547876-Chloro-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 86615232946119-30-8Yield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-chloro-5-fluoropyridine-6-carboxylic acid (2.00 g, 11.4 mmol), 41% aq. methylamine solution (8 mL) and 1,4-dioxane (8 mL) was heated at 125° C. under microwave irradiation for 60 min. After cooling, volatile material was distilled off, and the residue was dissolved in water (20 mL) and acidified to pH 3 by addition of 37% aq. hydrochloric acid solution. The precipitate was collected by filtration to produce the title compound (1.85 g, 87%). Light yellow solid, MS (ISP): 185.1 (M−H)−.

Workup

  1. temperatureAfter cooling
  2. distillationvolatile material was distilled off
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. additionacidified to pH 3 by addition of 37% aq. hydrochloric acid solution
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-86b46be19bb24e5fafc72b3f12c867ca
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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