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

HRID 878066

反応式

HRID 878066 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2f35d54c1af04d49ab672d4b138870de
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

関連ノート

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