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

HRID 1068216Notes

Reaction equation

HRID 1068216 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]>>[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

3

Reactant 2

HCID 198784-tert-ButylpyridineHCID 24533Sodium amide2×

Product 1

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

Conditions

Temperature
150 °C

Procedure

To 790 mg of sodium amide were added 20 mL of N,N-dimethylanaline and 2.74 g of 4-t-butyl pyridine at r.t. The mixture was stirred at 150° C. for 6 hours. During this period, 3 more portions of sodium amide (790 mg each) were added. The reaction was cooled down to r.t. The mixture was partitioned between EtOAc and water. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography with 50% EtOAc in hexanes followed by 100% EtOAc to give 1.68 g of the title compound as a solid: 1H NMR (500 MHz, CDCl3) δ1.21 (s, 9H), 4.55 (br, 2H) 6.44 (t, J=1.1 Hz, 1H), 6.62 (dd, J=5.5, 1.8 Hz, 1H), 7.94 (d, J=5.5Hz, 1H).

Workup

  1. waitDuring this period
  2. temperatureThe reaction was cooled down to r.t
  3. customThe mixture was partitioned between EtOAc and water
  4. extractionAqueous layer was extracted with EtOAc (3×)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-3b474fb256b34e6b8d6227696af3e1d6
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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