tert-Butanol → HCID 18382719, compound

HRID 1421245Notes

Reaction equation

HRID 1421245 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][N:4]=1)#[N:2].[C:11](O)([CH3:14])([CH3:13])[CH3:12].[OH-:16].[Na+]>OS(O)(=O)=O>[CH3:12][C:11]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[CH:5][N:4]=1)=[O:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 81672693,5-dimethylpyridine-2-carbonitrile

Product 1

HCID 18382719HCID 18382719, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 20.3 g (0.153 mol) of 2-cyano-3,5-dimethylpyridine in 100 mL of 20 mL of conc. H2SO4 within 10 minutes, followed by 20 mL of t-butanol over an additional 15 minutes. The solution was warmed at 75° C. for 30 minutes after which it was cooled to room temperature and basified with 25% NaOH. The product was extracted 3× with EtOAc (600 mL), which was combined and washed 1× with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (31.26 g) as a yellowish oil.

Workup

  1. extractionThe product was extracted 3× with EtOAc (600 mL), which
  2. washwashed 1× with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89f54dbc822e45ad9cf5fca2d4316d7b
Source dataset
uspto-grants-2000_06
Patent number
US06075025

Reaction notes

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