Sulfuric Acid → 3-Methylpyridine-2-carboxamide

HRID 60789

反応式

HRID 60789 の反応式
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:11].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][C:2]1[C:3]([C:8]([NH2:9])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 8199283-Methylpyridine-2-carbonitrile

生成物 1

HCID 166410233-Methylpyridine-2-carboxamide収率 97%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-methylpicolinonitrile (2.36 g, 20 mmol) and conc. sulfuric acid (12.5 mL) was stirred at 80° C. for 25 min. The solution was cooled to rt, poured into water (80 mL), followed by addition of sat. Na2CO3 (aq.) until pH ˜7. The resulting mixture was extracted with DCM (3×) and the combined organic layer was dried over MgSO4 and concentrated in vacuo to provide 3-methylpicolinamide as a white solid (2.65 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 8.43 (dd, 1H), 7.93 (brs, 1H), 7.62 (dd, 1H), 7.35 (dd, 1H), 5.44 (brs, 1H), 2.76 (s, 3H).

後処理

  1. temperatureThe solution was cooled to rt
  2. extractionThe resulting mixture was extracted with DCM (3×)
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-af1e112a241f4df6851c8639a4e9428b
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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