N,N-Dimethylaniline → 4-Cyclopropylpyridin-2-amine

HRID 1446703ノート

反応式

HRID 1446703 の反応式
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C[N:11](C)C1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=2)[CH2:3][CH2:2]1

参加物

6

反応物 2

HCID 949N,N-DimethylanilineHCID 36142304-Cyclopropylpyridine

生成物 1

HCID 457879154-Cyclopropylpyridin-2-amine収率 12%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Reflux 4-cyclopropyl-pyridine (600 mg, 5 mmol), N,N-dimethylaniline (1.4 mL, 11 mmol) and NaNH2 (50% in toluene, 468 mg, 6 mmol) at 150-160° C. under nitrogen in toluene for overnight. Cool the mixture and dilute with water and ethyl acetate. Extract the organic layer by minimal amount of water. Dry the organic layer (combination of anhydrous MgSO4, Na2SO4 and K2CO3), concentrate and purify by silica gel column chromatography to obtain the title compound in 12% yield. LCMS (ES), m/z 135 (M+1).

後処理

  1. temperatureCool the mixture
  2. extractionExtract the organic layer by minimal amount of water
  3. dry with materialDry the organic layer (combination of anhydrous MgSO4, Na2SO4 and K2CO3)
  4. concentrationconcentrate
  5. custompurify by silica gel column chromatography

出典と根拠

ORDレコード
ord-825403d65f1d46b1995ee4f8846e3bde
出典データセット
uspto-grants-2010_02
特許番号
US07666879B2

反応ノート

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