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

HRID 1446703Notes

Reaction equation

HRID 1446703 reaction equation
[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

Participants

6

Reactant 2

HCID 949N,N-DimethylanilineHCID 36142304-Cyclopropylpyridine

Product 1

HCID 457879154-Cyclopropylpyridin-2-amineYield 12%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-825403d65f1d46b1995ee4f8846e3bde
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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