Hydrochloric Acid → HCID 19088035, compound

HRID 1464511Notes

Reaction equation

HRID 1464511 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 and 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
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was crystallized

Sources & evidence

ORD record
ord-5e1e29c1e19c415b8fd0bee1741d4690
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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