Ammonium Hydroxide → 6-Isopropylpyridine-2,4-diol

HRID 895546Notes

Reaction equation

HRID 895546 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=O)[CH:3]=1.[NH4+:12].[OH-]>>[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[NH:12][C:4](=[O:5])[CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 546868844-hydroxy-6-(propan-2-yl)-2H-pyran-2-one

Product 1

HCID 546965906-Isopropylpyridine-2,4-diol

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxy-6-isopropyl-pyran-2-one (4.82 g, 31.3 mmol) in conc. NH4OH (15 mL) is stirred at 100° C. in a sealed tube for 4 h. The solution is then transferred to a recovery flask and concentrated in vacuo. Toluene is used to azeotropically remove any remaining water. 4-Hydroxy-6-isopropyl-1H-pyridin-2-one is obtained as a tan powder. 1H NMR (DMSO-d6, 300 MHz) δ 10.96 (br s, 1H), 10.36 (br s, 1H), 5.59 (d, J=2.1 Hz, 1H), 5.33 (d, J=2.1 Hz, 1H), 2.64 (sept, J=6.9 Hz, 1H), 1.11 (d, J=6.9 Hz, 6H) ppm.

Workup

  1. customThe solution is then transferred to a recovery flask
  2. concentrationconcentrated in vacuo
  3. customto azeotropically remove any remaining water

Sources & evidence

ORD record
ord-dec0cb0c0640480d8c560c282f4db47b
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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