1-Butanol → 4-(Pyridin-3-yl)pyridin-2-amine

HRID 40829

反応式

HRID 40829 の反応式
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[N+]([O-])(O)=O.[NH2:18][C:19]([NH2:21])=N.[OH-].[Na+].[CH2:24](O)CCC>>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2[CH:4]=[CH:3][N:18]=[C:19]([NH2:21])[CH:24]=2)[CH:8]=1

参加物

5

反応物 4

HCID 2631-ButanolHCID 10481Guanidine NitrateHCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

生成物 1

HCID 167414844-(Pyridin-3-yl)pyridin-2-amine収率 85%

実験手順

3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (15.4 g, 0.088 mol), guanidine nitrate (10.7 g, 0.088 mol), and sodium hydroxide (3.5 g, 0.088 mol) were dissolved in n-butanol (120 mL). The mixture was heated to reflux with stirring and maintained for 16 hours. The reaction mixture was then cooled to room temperature. The solid was collected and washed with water (400 mL). The desired product was dried under vacuum for three days and 12.7 g of yellow crystals of desired product was obtained (yield: 85%); 1H NMR (500 MHz, CDCl3) δ 5.15 (br., 2H), 7.09 (d, 1H), 7.44 (m, 1H), 8.33 (d, 1H), 8.42 (d, 1H), 8.73 (d, 1H), 9.22 (s, 1H). LC-MS (m/z) calculated, 172.2, found 173.2 [M+H]+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained for 16 hours
  4. customThe solid was collected
  5. washwashed with water (400 mL)
  6. dry with materialThe desired product was dried under vacuum for three days

出典と根拠

ORDレコード
ord-c87ada3ed37b452fbec27d14d79e9694
出典データセット
uspto-grants-2013_09
特許番号
US08530492B2

関連ノート

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