Ammonium Hydroxide → 2-Tert-butylpyridin-4(1H)-one

HRID 1469346Notes

Reaction equation

HRID 1469346 reaction equation
[C:1]([C:5]1O[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+:13]>>[C:1]([C:5]1[NH:13][CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 592936742-tert-butyl-4H-pyran-4-one

Product 1

HCID 582800252-Tert-butylpyridin-4(1H)-one

Procedure

A mixture of 2-tert-butyl-pyran-4-one (Step 1.6) (5.74 g, 37.7 mmol) and a 30% aqueous solution of ammonium hydroxide (100 mL) is stirred for 1 h at reflux, allowed to cool and concentrated. The residue is triturated with MeOH (200 mL) and filtered. The filtrate is concentrated and the residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1) to afford 4.46 g of the title compound as a yellow solid: ESI-MS: 152.0 [M+H]+; tR=1.45 min (System 1); TLC: Rf=0.11 (DCM/MeOH, 9:1).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. concentrationconcentrated
  4. customThe residue is triturated with MeOH (200 mL)
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1)

Sources & evidence

ORD record
ord-10a4226ae52e4ddc9e1f2abc69cda70b
Source dataset
uspto-grants-2015_04
Patent number
US09006270B2

Reaction notes

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