HCID 90273223, compound → HCID 90273273, compound

HRID 1050445Notes

Reaction equation

HRID 1050445 reaction equation
I[C:2]1[C:7](=[O:8])[C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[NH:4][C:3]=1[CH3:13].[Cu][C:15]#[N:16]>CN1CCCC1=O>[CH3:13][C:3]1[NH:4][C:5]([CH3:12])=[C:6]([N+:9]([O-:11])=[O:10])[C:7](=[O:8])[C:2]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 90273223HCID 90273223, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 90273273HCID 90273273, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3-iodo-2,6-dimethyl-5-nitropyridin-4(1H)-one (0.59 g, 2.006 mmol) and copper(I) cyanide (0.359 g, 4.01 mmol) in N-methyl-2-pyrrolidone (NMP) (10 mL) was heated at 125° C. for 2 h, at which time it was allowed to cool to ambient temperature and poured into ice/water/saturated NH4Cl (100 mL). The mixture was stirred for 15 min (pH˜6-7), then allowed to stand in an ice bath for 1 h. The solids were filtered, washed with a small amount of water, air dried for 10 min, and further dried in a vacuum oven at 37° C. for 18 h to give 2,6-dimethyl-5-nitro-4-oxo-1,4-dihydropyridine-3-carbonitrile (176 mg, 0.820 mmol, 40.9% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.30-2.38 (m, 3 H) 2.44-2.48 (m, 3 H) 12.78 (br. s., 1 H). MS(ES) [M+H]+ 193.9.

Workup

  1. temperatureto cool to ambient temperature
  2. waitto stand in an ice bath for 1 h
  3. filtrationThe solids were filtered
  4. washwashed with a small amount of water, air
  5. customdried for 10 min
  6. customfurther dried in a vacuum oven at 37° C. for 18 h

Sources & evidence

ORD record
ord-75094c48238d45c49038843ec98fc90c
Source dataset
uspto-grants-2016_07
Patent number
US09382234B2

Reaction notes

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