Hydrochloric Acid → HCID 19088035, compound

HRID 1646807Notes

Reaction equation

HRID 1646807 reaction equation
[N:1]1([C:6]2[CH:32]=[CH:31][C:9]([CH2:10][CH:11]([C:20]3[C:21](=[O:30])[C:22]([CH3:29])=[C:23]([CH3:28])[C:24](=[O:27])[C:25]=3[CH3:26])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl>C(O)(=O)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([C:20]3[C:21](=[O:30])[C:22]([CH3:29])=[C:23]([CH3:28])[C:24](=[O:27])[C:25]=3[CH3:26])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:31][CH:32]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19088029HCID 19088029, compound

Product 1

HCID 19088035HCID 19088035, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

In acetic acid (35 ml) was dissolved 3.50 g (8.06 mmole) of methyl 6-[4-(1-imidazolyl)benzyl]-6-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)hexanoate, and concentrated hydrochloric acid (16.1 ml) was added to the solution, followed by stirring at 100° C. for 1 hour. The solvent was distilled off, and acetone was added to the residue, followed by concentration under reduced pressure. The residue was chromatographed on a silica gel column, and elution was performed with chloroform/methanol (6:1). The fractions containing the object compound were collected nd concentrated under reduced pressure, and the residue was crystallized to give 2.94 g (87%) of 6-[4-(1-imidazolyl)benzyl]-6-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)hexanoic acid.

Workup

  1. additionwas added to the solution
  2. distillationThe solvent was distilled off
  3. additionacetone was added to the residue
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was chromatographed on a silica gel column, and elution
  6. additionThe fractions containing the object compound
  7. customwere collected nd
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was crystallized

Sources & evidence

ORD record
ord-17ee16ec5a254f49bbf4996b05459462
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

Loading…