Water → HCID 178487678, compound

HRID 531349Notes

Reaction equation

HRID 531349 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-f082f5fd7e4946cbbb57c29a7cb8913a
Source dataset
uspto-grants-2016_05
Patent number
US09353103B2

Reaction notes

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