Isopropanol → 2-Isopropoxy-6-methyl-nicotinonitrile

HRID 1505227Notes

Reaction equation

HRID 1505227 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH:13]([OH:16])([CH3:15])[CH3:14]>>[CH:13]([O:16][C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[C:8]([CH3:10])[N:9]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

Product 1

HCID 216043632-Isopropoxy-6-methyl-nicotinonitrile

Conditions

Temperature
50 °C

Procedure

The 2-chloro-6-methyl-nicotinonitrile (0.8 g, 5.2 mmol) was added in small portion to a mixture of NaH 60% (4 mol eq, 0.8 g) in isopropanol (30 mL). The reaction mixture was heated at 50° C. overnight. The solvent was distilled and water was added to the residue. The aqueous solution was extracted with EtOAc (3×30 mL) and the organic phases were evaporated at reduced pressure to give 32a as a pale yellow deliquescent solid (1.25 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 1.24 (s, 3H), 1.32 (s, 3H), 2.25 (s, 3H), 5.02 (m, 1H), 7.31 (d, 1H), 7.69 (m, 1H).

Workup

  1. distillationThe solvent was distilled
  2. additionwater was added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (3×30 mL)
  4. customthe organic phases were evaporated at reduced pressure

Sources & evidence

ORD record
ord-6a2ffe48f61e4f67b387598b3586deaf
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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