Hydrogen Bromide → 1-(3-Hydroxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone

HRID 2049656

Reaction equation

HRID 2049656 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:17])[CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[CH:7][CH:8]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]([C:9](=[O:17])[CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 203441421-(3-Methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone

Product 1

HCID 203441401-(3-Hydroxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

40.5 of 1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone are boiled under reflux for 6 hours with 180 ml of acetic acid and 180 ml of 47% hydrobromic acid. After concentration of the solution, the oily residue is brought to crystallization through treatment with 150 ml of hot ethanol. Cooling is allowed to take place, and 39.8 g (76% of theory) of the hydrobromide of the title compound is filtered off as greenish crystals: m.p. 165° to 168°.

Workup

  1. customAfter concentration of the solution, the oily residue is brought to crystallization through treatment with 150 ml of hot ethanol
  2. temperatureCooling
  3. filtrationis filtered off as greenish crystals

Sources & evidence

ORD record
ord-de4b1731d35c4d0a8b1e8f23c53058e2
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Linked notes

Loading…