Sodium ethoxide → 2-Ethoxy-6-methyl-5-nitronicotinonitrile

HRID 2407835Notes

Reaction equation

HRID 2407835 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].[O-:14][CH2:15][CH3:16].[Na+]>C(O)C.O.C(OCC)(=O)C>[CH2:15]([O:14][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])[CH3:16]

Participants

6

Reactant 2

HCID 2723922Sodium ethoxideHCID 132403822-Chloro-6-methyl-5-nitronicotinonitrile

Product 1

HCID 585042232-Ethoxy-6-methyl-5-nitronicotinonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the compound prepared in Example 443 (2.04 g) in ethanol (50 mL) at ambient temperature was added a 21% solution of sodium ethoxide in denatured ethanol (4.24 mL). The reaction mixture immediately turned dark purple and was stirred at ambient temperature for 2.5 hours, then diluted with water (250 mL), and the resulting mixture was stirred at ambient temperature for 3 days. The mixture was poured into a separatory funnel and diluted with water (250 mL) and ethyl acetate (500 mL). The organic layer was dried over sodium sulfate and concentrated to give about 9 g of a dark semisolid. This material was partitioned between dichloromethane (200 mL) and water (100 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 4/1 hexanes/ethyl acetate, to provide the title compound (0.87 g) with the following physical data.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 3 days
  2. additionThe mixture was poured into a separatory funnel
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f22ba06ab9174243ad526ef6fa679de8
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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