Water → HCID 178422951, compound

HRID 1692469Notes

Reaction equation

HRID 1692469 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](C)[C:7](OC)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].O.N1C=CC=C[CH:27]=1>>[OH:3][C:1]1[C:4]2[C:9](=[CH:8][C:7]([CH3:27])=[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 4

HCID 962WaterHCID 1049PyridineHCID 14797Potassium HydroxideHCID 579563966-Methylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methylphenyl)-amide

Product 1

HCID 178422951HCID 178422951, compoundYield 95%

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-bb13def65d3d4635976371049307d0e7
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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