Isopropanol → HCID 58873629, compound

HRID 1505213Notes

Reaction equation

HRID 1505213 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH:16]([OH:19])([CH3:18])[CH3:17]>>[CH:16]([O:19][C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrile

Product 1

HCID 58873629HCID 58873629, compoundYield 82%

Conditions

Temperature
50 °C

Procedure

The 2-chloro-6-trifluoromethyl-nicotinonitrile (0.5 g, 2.4 mmol) was added in small portion to a mixture of NaH 60% (4 mol eq) in isopropanol (20 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 (3×25 mL) and the organic phases were evaporated at reduced pressure to give e as a yellow solid (0.45 g, 82% Yield, 1.96 mmol). 1HNMR (DMSO, 200 MHz) δ 1.35 (s, 3H), 1.38 (s, 3H), 5.33 (m, 1H), 7.55 (d, 1H, J=6), 8.26 (d, 1H, J=6).

Workup

  1. distillationThe solvent was distilled
  2. additionwater was added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (3×25 mL)
  4. customthe organic phases were evaporated at reduced pressure

Sources & evidence

ORD record
ord-08f440dd6a7a47298ac009d6cd88c55a
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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