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

HRID 1408849Notes

Reaction equation

HRID 1408849 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-1aca5bbd587b4d80bd0b7afad4f660af
Source dataset
uspto-grants-2014_12
Patent number
US08921371B2

Reaction notes

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