Hydrochloric Acid → HCID 57656224, compound

HRID 911643Notes

Reaction equation

HRID 911643 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.Cl.[OH-].[Na+]>C1COCC1>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57656331HCID 57656331, compound

Product 1

HCID 57656224HCID 57656224, compoundYield 52,766.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 6-(3,3-dimethyl-butoxy)-nicotinonitrile (1.4 g, 6.86 mmol) in anhydrous THF (10 mL) under nitrogen and add 1M BH3-THF complex in THF (20.6 mL, 20.6 mmol). Stir the mixture overnight under nitrogen and then pour the reaction carefully into 5N aqueous HCl (20 mL). Stir the resulting suspension for 6 h at room temperature. Then basify by adding 2N aqueous NaOH (50 mL) and extract with dichloromethane (3×100 mL). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Take-up the resulting oil in methanol and filter it through an SCX column eluting with methanol followed by 3M ammonia in methanol. Concentrate in vacuo to obtain the title compound (754 g, 50%). GC-MS m/z: 208 (M>).

Workup

  1. additionpour
  2. stirringStir the resulting suspension for 6 h at room temperature
  3. extractionextract with dichloromethane (3×100 mL)
  4. dry with materialDry the combined organic extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. filtrationfilter it through an SCX column
  8. washeluting with methanol
  9. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-ff5890989d4b4146a3d0d1a74d0d4d15
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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