N-[4-chloro-2-(hydroxy-pyridin-3-yl-methyl)-phenyl]-2,2-dimethyl-propionamide → N-[4-Chloro-2-(pyridine-3-carbonyl)phenyl]-2,2-dimethylpropanamide

HRID 730095Notes

Reaction equation

HRID 730095 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH:15]([OH:22])[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:3]=1>N1C=CC=CC=1.CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:22])[CH:3]=1

Participants

4

Reactant 1

HCID 22327296N-[4-chloro-2-(hydroxy-pyridin-3-yl-methyl)-phenyl]-2,2-dimethyl-propionamide

Product 1

HCID 14141153N-[4-Chloro-2-(pyridine-3-carbonyl)phenyl]-2,2-dimethylpropanamideYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 22728543Water ethylacetateSolvent

Procedure

N-[4-chloro-2-(hydroxy-pyridin-3-yl-methyl)-phenyl]-2,2-dimethyl-propionamide (1.0 g, 3.14 mmol) was dissolved in 5 mL pyridine and treated with CrO3 (0.75 g, 7.5 mmol, 2.39 eq). The mixture was stirred under N2 at room temperature for five hours, diluted with 20 mL 1:2 EtOAc/H2O, and filtered through Celite. The aqueous phase was separated and discarded, then the organics dried under vacuum yielding product (680 mg, 70%). 1H NMR (CDCl3) δ 11.06 (s, 1H) 8.92 (d, J=2.4 Hz, 1H) 8.84 (d, J=8.0 Hz, 1H) 8.73 (d, J=9.2 Hz, 1H) 8.00 (d, J=8.0 Hz, 1H) 7.56 (dd, J=11.2 Hz, 2.0 Hz, 1H) 7.48 (m, 2H) 1.36 (s, 9H) MS (ES) m/z=317.1 (MH)+

Workup

  1. filtrationfiltered through Celite
  2. customThe aqueous phase was separated
  3. customthe organics dried under vacuum

Sources & evidence

ORD record
ord-34e5ebb188cb4d23bccf4dfd06698e18
Source dataset
uspto-grants-2009_09
Patent number
US07582661B2

Reaction notes

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