Dimethylformamide → HCID 22591412, compound

HRID 707346Notes

Reaction equation

HRID 707346 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]1([NH2:18])[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[N+:8]([C:7]1[C:2]([NH:17][CH:14]2[CH2:15][CH2:16][CH:11]([NH2:18])[CH2:12][CH2:13]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 183741,4-DiaminocyclohexaneHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 22591412HCID 22591412, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-3-nitropyridine (10 g, 63.3 mmol), cyclohexane-1,4-diamine (7.2 g, 63.3 mmol), anhydrous dimethylformamide (100 mL) and anhydrous sodium carbonate (13.4 g, 126 mmol) were combined with stirring under nitrogen. The reaction mixture was stirred at room temperature for 14 hours. It was poured into water and the resulting orange solid was filtered off and found to be N1-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine (8.2 g, 34.7 mmol, 54.9% yield) which was used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 14 hours
  2. filtrationthe resulting orange solid was filtered off

Sources & evidence

ORD record
ord-abbecd35ebca496e94550dea5151c2dd
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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