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

HRID 2133

반응식

HRID 2133 반응식
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[OH:10]S(O)(=O)=O.[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:10])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

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

생성물 1

HCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamide수율 97%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
70 °C

실험 절차

Suspend 2-cyano-3-methyl pyridine (400 g) in t-butanol (800 mL) and heat to 70° C. Add concentrated H2SO4 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-07e514fe010d477b830fbb79e7963a40
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728703

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