Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

HRID 21412

反応式

HRID 21412 の反応式
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].S(=O)(=O)(O)[OH:11].[C:15]1([CH3:21])[CH:20]=CC=C[CH:16]=1.N>C(O)(C)(C)C.O>[CH3:16][C:15]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:11])([CH3:21])[CH3:20]

参加物

7

反応物 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 1140TolueneHCID 8199283-Methylpyridine-2-carbonitrile

生成物 1

HCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamide収率 97%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
70 °C

実験手順

Suspend 2-cyano-3-methyl pyridine (400 g) in t-butanol (800 mL) and heat to 70° C. Add concentrated sulphuric acid (400 mL) dropwise over 45 minutes. Maintain the temperature at 75° C., until the reaction is complete, and for an additional 30 minutes. Dilute the mixture with water (400 mL), charge with toluene (600 mL) and bring to pH 10 with concentrated aqueous ammonia. Maintain the temperature at 50°-55° C. during the work up. Separate the toluene phase, and reextract the aqueous layer. Combine toluene phases and wash with water. Remove the toluene to yield the title compound N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide, as an oil, from which solid product is crystallized. (Yield 97%, as determined by an internal standard assay with gas chromatography).

後処理

  1. temperatureMaintain the temperature at 75° C.
  2. temperatureMaintain the temperature at 50°-55° C. during the work up
  3. customSeparate the toluene phase
  4. washCombine toluene phases and wash with water
  5. customRemove the toluene

出典と根拠

ORDレコード
ord-97f4665705e544efbed0da4605e8a7f7
出典データセット
uspto-grants-1995_06
特許番号
US05422351

関連ノート

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