Ammonia → HCID 70819321, compound

HRID 512085Notes

Reaction equation

HRID 512085 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])O[C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH3:17]>>[CH2:1]([C:8]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[NH:17][C:9]=1[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86710142HCID 86710142, compound

Product 1

HCID 70819321HCID 70819321, compound

Procedure

Compound 1 (0.01 g, 30.6 mmol) was heated at 100° C. with aqueous ammonia in a high pressure tube for 18 h. After the mixture was cooled to room temperature, the crude was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with 5:1 ethyl acetate/methanol gave 3-heptyl-2,6-dimethylpyridin-4(1H)-one (3) as a brown solid: yield 0.083 g (81%); silica gel TLC Rf 0.25 (3:1 ethyl acetate/methanol); 1H NMR (CD3OD) δ 0.68-0.71 (m, 3H), 1.09-1.28 (m, 10H), 2.20 (s, 3H), 2.27 (s, 3H), 2.34-2.36 (m, 2H) and 6.29 (s, 1H).

Workup

  1. concentrationthe crude was concentrated under diminished pressure
  2. customThe residue was purified by chromatography on a silica gel column
  3. washElution with 5:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-6d404df9f5004e53987c7ecd04e375a6
Source dataset
uspto-grants-2015_08
Patent number
US09102626B2

Reaction notes

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