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

HRID 2066784Notes

Reaction equation

HRID 2066784 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

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 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 1.6) (66.6 mmol) and a 28-30% aqueous solution of ammonium hydroxide (182 mL) was stirred for 1 h at 65° C. After cooling to rt, the reaction mixture was decanted to remove a dark brown solid and then concentrated. The residue was diluted with MeOH and re-concentrated (3×) to afford the title compound as a brown-orange solid. HPLC: tR=3.56 min (method B); LC-MS: tR=0.87 min, [M+H]+ 151; TLC: Rf=0.18 (9:1 CH2Cl2/MeOH).

Workup

  1. customthe reaction mixture was decanted
  2. customto remove a dark brown solid
  3. concentrationconcentrated
  4. additionThe residue was diluted with MeOH
  5. concentrationre-concentrated (3×)

Sources & evidence

ORD record
ord-8be7b91bf069441195fde5d3549a121e
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

Loading…