Water → HCID 178487677, compound

HRID 1685869Notes

Reaction equation

HRID 1685869 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)=O)=[C:8]([CH3:22])[C:7]([O:23][CH3:24])=[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]([CH3:22])[C:7]([O:23][CH3:24])=[CH:6][CH:5]=2)[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 579564066-Isopropylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methyl-phenyl)amide

Product 1

HCID 178487677HCID 178487677, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
133 °C

Procedure

To a solution of 6-isopropylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methyl-phenyl)amide (107, 0.70 g, 2.14 mmol) in pyridine (5 mL) were added 2.5 equivalents of freshly grounded KOH along with water (50 μL). The mixture was heated by microwave irradiation at 133° C. for 55 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 0.62 g (95%) of the title compound 108 (1.8 g, 95%): m/z=309 (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-9f6efbb9d52c46eaa2d7f11aee2a107e
Source dataset
uspto-grants-2012_04
Patent number
US08148399B2

Reaction notes

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