4-tert-Butylpyridine → 4-(tert-Butyl)pyridin-2-amine

HRID 278242Notes

Reaction equation

HRID 278242 reaction equation
[NH2-:1].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>CN(C)C1C=CC=CC=1>[NH2:1][C:9]1[CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 198784-tert-ButylpyridineHCID 24533Sodium amide2×

Product 1

HCID 123519414-(tert-Butyl)pyridin-2-amineYield 55.2%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
150 °C

Procedure

To 790 mg of sodium amide were added 20 mL of N,N-dimethylaniline and 2.74 g of 4-t-butyl pyridine at rt. The mixture was stirred at 150° C. for 6 h. During this period, 3 more portions of sodium amide (790 mg each) were added. The reaction was cooled down to rt. The mixture was partitioned between ethyl acetate and water. Aqueous layer was extracted with ethyl acetate (3×). The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography with 50% ethyl acetate in hexanes followed by 100% ethyl acetate to give 1.68 g of the title compound as a solid:

Workup

  1. waitDuring this period
  2. temperatureThe reaction was cooled down to rt
  3. customThe mixture was partitioned between ethyl acetate and water
  4. extractionAqueous layer was extracted with ethyl acetate (3×)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dec5f9f7e10e478993705500356ab360
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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