Ammonia → HCID 70819248, compound

HRID 1051143Notes

Reaction equation

HRID 1051143 reaction equation
[CH2:1]([C:17]1[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])O[C:18]=1[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH3:26]>>[CH2:1]([C:17]1[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[NH:26][C:18]=1[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86710145HCID 86710145, compound

Product 1

HCID 70819248HCID 70819248, compound

Procedure

Compound 2 (0.02 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-hexadecyl-2,6-dimethylpyridin-4(1H)-one (4) as a brown solid; yield 0.01 g (51%); silica gel TLC Rf 0.25 (3:1 ethyl acetate/methanol); 1H NMR (CDCl3, 400 MHz) δ 0.88-0.89 (m, 3H), 1.28-1.32 (m, 28H), 2.28 (s, 3H), 2.34 (s, 3H), 2.44-2.47 (m, 2H) and 6.18 (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-d59cb599469d4b008e802bc70a653925
Source dataset
uspto-grants-2016_07
Patent number
US09388163B2

Reaction notes

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