Ethyl Acetate → 4-(5-Chloro-2-methyl-phenyl)-pyridin-3-ylamine

HRID 878066

Reaction equation

HRID 878066 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14]C(=O)C(C)(C)C)[CH:7]=1.[OH-].[Na+].CCOC(C)=O>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70663288N-[4-(5-chloro-2-methyl-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide

Product 1

HCID 706633654-(5-Chloro-2-methyl-phenyl)-pyridin-3-ylamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[4-(5-chloro-2-methyl-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide (1 g, 3.3 mmol) in 3M aqueous HCl (50 mL) was stirred at 90° C. for 18 hours. The reaction mixture was poured on 200 mL 1M aqueous NaOH solution and 150 mL EtOAc. The layers were separated and the aqueous layer was extracted a second time with 150 mL EtOAc. The combined organic layers were washed with 150 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Light brown viscous oil (720 mg, 99%). MS (ESI): m/z=219.068 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted a second time with 150 mL EtOAc
  3. washThe combined organic layers were washed with 150 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2f35d54c1af04d49ab672d4b138870de
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Linked notes

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