Cyclohexylamine → 6-chloro-N-cyclohexyl-3-nitropyridin-2-amine

HRID 1890347Notes

Reaction equation

HRID 1890347 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:18][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 431526936-chloro-N-cyclohexyl-3-nitropyridin-2-amineYield 32.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

2,6-Dichloro-3-nitropyridine (5 g, 25.9 mmol) and cyclohexanamine (5.14 g, 51.8 mmol) were added to ethanol (17.5 mL). The reaction mixture was heated at 140° C. by microwave irradiation for 3 h. A yellow solid precipitated out. The solid was filtered, washed with cold ethanol, and dried under vacuum to afford the title compound (2.162 g) without further purification. LCMS m/z=256.40 [M+H]+.

Workup

  1. customA yellow solid precipitated out
  2. filtrationThe solid was filtered
  3. washwashed with cold ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e61ae8b9bb3946d5a4d7b0542cfdc363
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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