Hydrogen Bromide → 2,3-Dihydro-5-phenyl-4-benzofuranamine

HRID 617409Notes

Reaction equation

HRID 617409 reaction equation
OC[CH2:3][C:4]1[C:5]([NH:18]C(=O)C(C)(C)C)=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Br>O>[C:12]1([C:6]2[C:5]([NH2:18])=[C:4]3[CH2:3][CH2:11][O:10][C:9]3=[CH:8][CH:7]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21852186N-[3-(2-Hydroxyethyl)-4-methoxy-[1,1'-biphenyl]-2-yl]-2,2-dimethylpropanamide

Product 1

HCID 218521822,3-Dihydro-5-phenyl-4-benzofuranamineYield 28.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A pressure bottle was charged with N-[3-(2-hydroxyethyl)-4-methoxy-[1,1'-biphenyl]-2-yl]-2,2-dimethylpropanamide (10.77 g, 32.9 mmol), 48% HBr solution (200 mL), flushed with nitrogen, capped, and stirred at 95° C. for 12 h. The suspension was cooled to room temperature and poured over 200 g of ice/water. The aqueous phase was washed with Et2O (2×100 mL) and concentrated in vacuo to give a tan solid. The solid was redigested with H2O (200 mL), concentrated in vacuo, and dried (0.5 mm, 18 h). The resultant solid was digested with 1 N NaOH (300 mL), the resultant suspension extracted with CH2Cl2 (3×300 mL), and the combined extracts dried (K2CO3), filtered, and concentrated in vacuo to give the free amine (2.01 g, 21%) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.05 (t, J=8.5 Hz, 2H), 4.64 (t, J=8.5 Hz, 2H), 6.34 (d, J=8 Hz, 1H), 6,91 (d, J=8 Hz, 1H), 7.29-7.45 (m, 7H).

Workup

  1. customflushed with nitrogen
  2. customcapped
  3. temperatureThe suspension was cooled to room temperature
  4. additionpoured over 200 g of ice/water
  5. washThe aqueous phase was washed with Et2O (2×100 mL)
  6. concentrationconcentrated in vacuo
  7. customto give a tan solid
  8. concentrationconcentrated in vacuo
  9. customdried (0.5 mm, 18 h)
  10. extractionthe resultant suspension extracted with CH2Cl2 (3×300 mL)
  11. dry with materialthe combined extracts dried (K2CO3)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-708306ee5ced4514b3d3688080b6feff
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

Loading…