Hydrogen Bromide → HCID 20265971, compound

HRID 1719865Notes

Reaction equation

HRID 1719865 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.Br.O>C(O)(=O)C>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 20265982HCID 20265982, compound

Product 1

HCID 20265971HCID 20265971, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Methoxy-1-pyrrolidinyl-naphthalene (90 g) is dissolved in glacial acetic acid (1 liter). 48% hydrobromic acid is added to the solution and the resulting reaction mixture heated to reflux for 3 hours. The reaction mixture is poured into water and crushed ice and the solution made alkaline to pH 8 to 9. The aqueous mixture is extracted with methylene chloride. The methylene chloride extract is back-extracted with 2% KOH solution and the combined basic layers made acidic by the addition of aqueous HCl. The addition is continued until a white precipitate appears. The aqueous solution is extracted with methylene chloride and the organic layer washed with H2O, dried, filtered and evaporated in vacuo, yielding the desired product.

Workup

  1. customthe resulting reaction mixture
  2. temperatureheated
  3. temperatureto reflux for 3 hours
  4. customcrushed ice
  5. extractionThe aqueous mixture is extracted with methylene chloride
  6. extractionThe methylene chloride extract
  7. extractionis back-extracted with 2% KOH solution
  8. additionthe combined basic layers made acidic by the addition of aqueous HCl
  9. additionThe addition
  10. extractionThe aqueous solution is extracted with methylene chloride
  11. washthe organic layer washed with H2O
  12. customdried
  13. filtrationfiltered
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-73181afc784f42ce9730ad2869044c0d
Source dataset
uspto-grants-1985_09
Patent number
US04543352

Reaction notes

Loading…