Potassium Carbonate → 2-[N-(cyclopentylmethyl)-N-ethylamino]-6-methyl-5-nitronicotinonitrile

HRID 1960049Notes

Reaction equation

HRID 1960049 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH:14]1([CH2:19][NH:20][CH2:21][CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH:14]1([CH2:19][N:20]([C:2]2[N:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=2[C:4]#[N:5])[CH2:21][CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132403822-Chloro-6-methyl-5-nitronicotinonitrileHCID 43163716N-(cyclopentylmethyl)-N-ethylamine

Product 1

HCID 578612722-[N-(cyclopentylmethyl)-N-ethylamino]-6-methyl-5-nitronicotinonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-6-methyl-5-nitronicotinonitrile (997 mg, 5.05 mmol), N-(cyclopentylmethy)-N-ethylamine (770 mg, 6.05 mmol), and K2CO3 (1.7 g, 12.3 mmol) in toluene (20 mL) is heated to 110° C. After stirring for 3 hours, the reaction mixture is filtered to remove the resulting precipitate. The filtrate is diluted with EtOAc and washed with H2O and brine. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica-gel column chromatography to give 2-[N-(cyclopentylmethyl)-N-ethylamino]-6-methyl-5-nitronicotinonitrile as orange oil.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customto remove the resulting precipitate
  3. additionThe filtrate is diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-834127d8f7a34d328635d03d1f6cb8fd
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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