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

HRID 1516211Notes

Reaction equation

HRID 1516211 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-2cf0ca3585804b85be92ea2dbb6c3d8c
Source dataset
uspto-grants-2012_07
Patent number
US08227462B2

Reaction notes

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