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

HRID 874065Notes

Reaction equation

HRID 874065 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-06dc7a16eb36422c954bc1c9d147b9a9
Source dataset
uspto-grants-2015_03
Patent number
US08980259B2

Reaction notes

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