Water → HCID 178487678, compound

HRID 579638Notes

Reaction equation

HRID 579638 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)=O)=[C:8]([CH3:20])[C:7]([O:21][CH3:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].O>N1C=CC=CC=1>[OH:3][C:1]1[C:4]2[C:9](=[C:8]([CH3:20])[C:7]([O:21][CH3:22])=[CH:6][CH:5]=2)[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 579563966-Methylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methylphenyl)-amide

Product 1

HCID 178487678HCID 178487678, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-methylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methyl-phenyl)-amide (96) in pyridine (15 mL) was added 2.5 equivalent of freshly grounded KOH along with water (200 μL). The mixture was heated by microwave irradiation at 150° C. for 30 min, then 80-85% of the pyridine was evaporated under reduced pressure. The residue was poured on ice and neutralized with acetic acid. The precipitate was filtered off, then dried to give the title compound (1.8 g, 95%): m/z=299 (M+H)+.

Workup

  1. custom80-85% of the pyridine was evaporated under reduced pressure
  2. additionThe residue was poured on ice and neutralized with acetic acid
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-f377f860dd03462abf222727e969ead6
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

Loading…