Water → N,N-diethyl-2-[(4-methylpyridin-3-yl)amino]nicotinamide

HRID 75198

反応式

HRID 75198 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].Cl[C:10]1[N:22]=[CH:21][CH:20]=[CH:19][C:11]=1[C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13].[H-].[Na+].O>O1CCOCC1>[CH2:17]([N:14]([CH2:15][CH3:16])[C:12](=[O:13])[C:11]1[CH:19]=[CH:20][CH:21]=[N:22][C:10]=1[NH:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:18]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1379353-Amino-4-picolineHCID 44659442-Chloro-N,N-diethylnicotinamide

生成物 1

HCID 66886620N,N-diethyl-2-[(4-methylpyridin-3-yl)amino]nicotinamide収率 84.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Into a 1-neck round-bottom flask was added 4-methylpyridin-3-amine (1.02 g, 0.00940 mol) and 2-chloro-N,N-diethylnicotinamide (2.00 g, 0.00940 mol) in 1,4-dioxane (20 mL), and then sodium hydride (0.94 g, 0.024 mol) was added. The reaction was heated at reflux for 1 hour. The mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate 3× and the combined organic extracts were washed with water, brine, dried over MgSO4, and concentrate in vacuo. Upon cooling, the product crystallized. The crystalline solid was filtered off, washed with ether and dried to give 2.27 g of the desired product. 1H NMR (300 MHz, CDCl3): δ 9.15 (s, 1H), 8.21-8.24 (m, 2H), 7.90 (br s, 1H), 7.47 (dd, 1H J1=7.5, J2=1.8 Hz), 7.11 (d, 1H, J=4.8 Hz), 6.75 (dd, 1H, J1=7.5, J2=5.1 Hz), 3.46-3.51 (m, 4H), 2.29 (s, 3H), 1.25 (t, 6H). MS [M+1]=285.

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. extractionThe mixture was then extracted with ethyl acetate 3×
  5. washthe combined organic extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrate in vacuo
  8. temperatureUpon cooling
  9. customthe product crystallized
  10. filtrationThe crystalline solid was filtered off
  11. washwashed with ether
  12. customdried

出典と根拠

ORDレコード
ord-64ff0fe9c8d645dbbb29c3f35689905c
出典データセット
uspto-grants-2014_09
特許番号
US08835423B2

関連ノート

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