2-(2-Chlorophenyl)ethylamine → 2-Amino-5-cyanopyridine

HRID 1720907Notes

Reaction equation

HRID 1720907 reaction equation
C([N:3]=[C:4]([C:9]1[CH:10]=[N:11][C:12]([NH2:15])=[CH:13][CH:14]=1)OCCC)#N.ClC1C=CC=CC=1CCN>CO.CN(C=O)C>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([C:4]#[N:3])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 22416550HCID 22416550, compound

Product 1

HCID 8182602-Amino-5-cyanopyridineYield 214.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1H-NMR (500 MHz, DMSO): δ (ppm). 8.74(1H, d, J=2.4Hz, H-6), 8.04(1H, dd, J=2.4, 9.2Hz, H-4), 7.20(1H, brs, NH2), 6.53(1H, d, J=9.2Hz, H-3 ) , 4.27 (2H, t, J=6.7Hz, OCH2CH2CH3), 1.7 5 (2H, m, OCH2CH2CH3) , 0.97 (3H, t, J=7.3Hz, OCH2CH2CH3). Propyl N-cyano-6-amino-3-pyridinecarboximidate (200 mg, 0.98 mmol) and 2-(2-chlorophenyl)ethylamine (170 mg, 1.09 mmol) were dissolved in a mixture of methanol (10 ml) and DMF (1.5 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and subjected to silica gel column chromatography (Wako Gel C-200, 25 g), and elution was conducted with chloroform:methanol (30:1) to give the title compound (250 mg, yield 85%) as colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washsubjected to silica gel column chromatography (Wako Gel C-200, 25 g), and elution

Sources & evidence

ORD record
ord-9f5b4180cda542e9bbe7b810dee9307a
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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