Cyclopropylamine → N-Cyclopropyl-3-nitropyridin-4-amine

HRID 2170986Notes

Reaction equation

HRID 2170986 reaction equation
CO[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:15])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(O)C>[CH:12]1([NH:15][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N+:9]([O-:11])=[O:10])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 3558324-Methoxy-3-nitropyridine

Product 1

HCID 22349359N-Cyclopropyl-3-nitropyridin-4-amineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxy-3-nitropyridine 5-a (CAS 31872-62-5) (200 g, 1300 mmol), cyclopropyl-amine (CAS 765-30-0) (185.5 g, 3250 mmol) and DIEA (CAS 7087-68-5) (336 g, 2600 mmol) in dry ethanol (800 mL) was refluxed for 3 hours. The mixture was cooled to 0° C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford compound 5-b as a white powder (167 g, 72%).

Workup

  1. filtrationThe solid was collected by filtration
  2. washThe filter cake was washed with cold ethanol (150 mL)
  3. customThe solid was dried

Sources & evidence

ORD record
ord-e96780680f844076b2471ccc08417f00
Source dataset
uspto-grants-2015_06
Patent number
US09051317B2

Reaction notes

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