Ammonium Hydroxide → 2-(1-Methylcyclopropyl)pyridin-4(1H)-one

Reaction equation

[CH3:1][C:2]1([C:5]2O[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=2)[CH2:4][CH2:3]1.[OH-].[NH4+:13]>>[CH3:1][C:2]1([C:5]2[NH:13][CH:7]=[CH:8][C:9](=[O:11])[CH:10]=2)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 574170892-(1-Methylcyclopropyl)-4H-pyran-4-one

Product 1

HCID 552861162-(1-Methylcyclopropyl)pyridin-4(1H)-one

Procedure

A mixture of 2-(1-methyl-cyclopropyl)-pyran-4-one (Step 40.6) (440 mg, 2.93 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 purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1) to afford 333 mg of the title compound as a yellow solid: ESI-MS: 150.0 [M+H]+; tR=1.25 min (System 1).

Workup

temperatureat reflux
temperatureto cool
concentrationconcentrated
customThe residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1→92:7:1)

Sources & evidence

ORD record: ord-7c629a8c8b4e433bba04096ea5fe76ce
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940771B2

Reaction notes

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