N,N-Dimethylaniline → 4-(tert-Butyl)pyridin-2-amine

HRID 1910352Notes

Reaction equation

HRID 1910352 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2-].[Na+].C[N:14](C)C1C=CC=CC=1>C(OCC)(=O)C>[NH2:14][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 198784-tert-ButylpyridineHCID 24533Sodium amide

Product 1

HCID 123519414-(tert-Butyl)pyridin-2-amineYield 45.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To 100 g (0.73 mol) of 4-tert-butyl-pyridine and 31.0 g (0.79 mol) of sodium amide was added 181 mL (1.5 mol) of N,N,-dimethylaniline. The reaction mixture was heated with stirring under nitrogen for 7 hours at 150° C. After cooling, the reaction mixture was added to 400 mL of ice. ˜250 mL of ethyl acetate was added to the mixture to extract the organic phase. The organic phase was evaporated and fractional distilled. About ˜50 g (45% yield) of 2-amino-4-tert-butylpyridine was obtained. MS results confirmed the desired products.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureAfter cooling
  3. extractionto extract the organic phase
  4. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-00e77a8a8791477983002b9f71c4eb08
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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