Triethylamine → 2,2-dimethyl-N-(pyridin-3-yl)propanamide

HRID 7776

反応式

HRID 7776 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15])[CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 62493Pivaloyl chloride

生成物 1

HCID 46550442,2-dimethyl-N-(pyridin-3-yl)propanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 3-aminopyridine (9.41 g, 100 mmol) and triethylamine (16.7 mL, 120 mmol) in CH2Cl2 (300 mL) at 0° C. was added trimethylacetyl chloride (14.8 mL, 120 mmol) dropwise over 15 min. The reaction was warmed to rt and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned between EtOAc and H2O, and the layers separated. The aqueous layer was made basic with saturated NaHCO3 and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-(pyridin-3-yl)-2,2-dimethylpropanamide as a tan solid. 1H NMR (CDCl3, 300 MHz) δ 8.57 (d, 1H), 8.33 (dd, 1H), 8.17 (ddd, 1H), 7.69 (br s, 1H), 7.27 (dd, 1H), 1.33 (s, 9H).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. customthe layers separated
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with saturated NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-640654338223404497e09faf1387ac75
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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