Sodium Hydroxide → (2-Amino-5-chlorophenyl)(pyridin-3-yl)methanone

HRID 29505Notes

Reaction equation

HRID 29505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C(C)(C)C)=[C:4]([C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:3]=1.[OH-].[Na+]>OS(O)(=O)=O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14141153N-[4-Chloro-2-(pyridine-3-carbonyl)phenyl]-2,2-dimethylpropanamide

Product 1

HCID 13549723(2-Amino-5-chlorophenyl)(pyridin-3-yl)methanoneYield 77.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
95 °C

Procedure

N-[4-chloro-2-(pyridine-3-carbonyl )-phenyl]-2,2-dimethyl-propionamide (0.65 g) was suspended in 5 mL of 70% H2SO4 and heated at 95° C. in oil bath overnight. After cooling to room temperature the solution was added drop wise with stirring to 20 mL of 40% NaOH solution placed in an ice-water bath. The fine yellow precipitate formed was collected by vacuum filtration, washed well with water and dried under vacuum to give 370 mg of product. 1H NMR (CDCl3) δ 8.84 (dd, J=2.4 Hz, 0.8 Hz, 1H) 8.77 (dd, J=4.8 Hz, 2.0 Hz, 1H) 7.93 (dt, J=8.4 Hz, 2.0 Hz, 1H) 7.43 (m, 1H) 7.35 (d, J=2.0 Hz, 1H) 7.25 (d, J=0.8 Hz, 1H) 6.71 (d, J=8.8 Hz, 1H) 6.21 (s, 2H) MS (ES) m/z=233.0 (MH)+

Workup

  1. temperatureAfter cooling to room temperature the solution
  2. additionwas added drop wise
  3. customplaced in an ice-water bath
  4. customThe fine yellow precipitate formed
  5. filtrationwas collected by vacuum filtration
  6. washwashed well with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c22db33c4fd34ed0bbf17391fb3b5ef8
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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