Pyridine-2-carbonitrile → 3,4-Dimethoxyphenyl 2-pyridyl ketone

HRID 1017949Notes

Reaction equation

HRID 1017949 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([C:8]1[CH:13]=[CH:12]N=CC=1)=[O:7].[C:19]([C:21]1C=CC=CN=1)#[N:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:6]([C:8]1[CH:13]=[CH:12][CH:21]=[CH:19][N:20]=1)=[O:7]

Participants

3

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 215846084-(3,4-Dimethoxybenzoyl)pyridine

Product 1

HCID 1197013,4-Dimethoxyphenyl 2-pyridyl ketone

Procedure

2-(3,4-Dimethoxybenzoyl)pyridine was prepared analogously to 4-(3,4-dimethoxy-benzoyl)pyridine using 2-cyanopyridine. The crude mixture was purified by flash column chromatography (silica gel, 1% methanol/methylene chloride) to afford after drying in vacuo (60° C., 1 mm) 1.67 g (34%) of the product: mp 91.5-93° C.; 1H NMR (CDCl3) δ 8.76-8.70 (m, 1 H), 8.05-7.71 (m, 4 H), 7.55-7.45 (m, 1 H), 7.00-6.89 (m, 1 H), 3.96 (s, 3 H), 3.96 (s, 3 H); 13C NMR (CDCl3) δ 192.1, 155.7, 153.3, 148.7, 148.2, 136.9, 128.9, 126.7, 125.7, 124.4, 112.6, 109.8, 56.0, 55.9; Anal. Calcd for C14H13NO3. Theoretical: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.96; H, 5.47; N, 5.66.

Workup

  1. customThe crude mixture was purified by flash column chromatography (silica gel, 1% methanol/methylene chloride)
  2. customto afford
  3. dry with materialafter drying in vacuo (60° C., 1 mm) 1.67 g (34%) of the product

Sources & evidence

ORD record
ord-559e0962786c41c9938a0260d29f188a
Source dataset
uspto-grants-2002_11
Patent number
US06479554B2

Reaction notes

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