2-Nitroacetamide → 6-Cyclopropyl-3-nitropyridin-2-ol

HRID 1600071

Reaction equation

HRID 1600071 reaction equation
CN([CH:4]=[CH:5][C:6]([CH:8]1[CH2:10][CH2:9]1)=O)C.[N+:11]([CH2:14][C:15]([NH2:17])=[O:16])([O-:13])=[O:12].C([O-])(=O)C.[NH2+]1CCCCC1>O>[CH:8]1([C:6]2[NH:17][C:15](=[O:16])[C:14]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 2792562-NitroacetamideHCID 3014295Piperidinium acetateHCID 70176771-Cyclopropyl-3-(dimethylamino)prop-2-en-1-one

Product 1

HCID 220087796-Cyclopropyl-3-nitropyridin-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of crude β-N,N-dimethylaminoethenylcyclopropyl ketone (12 g, <86 mmol), nitroacetamide (9 g, 86 mmol) and aqueous piperidinium acetate (10 ml) [prepared from glacial acetic acid (42 ml), water (100 ml) and piperidine (72 ml)] was stirred at room temperature overnight. Following dilution with water (20 ml), the yellow precipitate was isolated via filtration and drying in vacuo to yield 5.30 g of the title compound: 1H NMR (CDCl3) δ1.15 (m, 2 H), 1.36 (m, 2 H), 2.10 (m, 1 H), 6.02 (br d, J=8.0Hz, 1 H), 8.41 (d, J=8.0 Hz, 1 H).

Workup

  1. customthe yellow precipitate was isolated via filtration
  2. customdrying in vacuo

Sources & evidence

ORD record
ord-c690855e6b1540f2b5227ddf18488d70
Source dataset
uspto-grants-1998_04
Patent number
US05744486

Linked notes

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