Hydrochloric Acid → HCID 11403801, compound

HRID 1372178Notes

Reaction equation

HRID 1372178 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:14].[ClH:15]>O>[Cl:15][C:10]1[C:9]2[O:12][CH2:13][C:7]3[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:6]=3[C:8]=2[CH:7]=[C:6]2[CH:5]=[CH:4][C:3]([OH:14])=[CH:2][C:11]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12808088HCID 12808088, compound

Product 1

HCID 11403801HCID 11403801, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 9 (2.25 g, 6.92 mmol) and pyridiumium hydrochloride (21.9 g, 162 mmol) was heated to 184° C. for 2 hrs. The reaction mixture was allowed to cool and poured into water (300 mL) and extracted with ethyl acetate (2×200 mL), washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed and the product was chromatographed (40% ethyl acetate-hexanes) to afford a white solid which was triturated with methylene chloride (25 mL) to afford 1.2 g (58%); mp 230–231° C.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe product was chromatographed (40% ethyl acetate-hexanes)
  7. customto afford a white solid which
  8. customwas triturated with methylene chloride (25 mL)
  9. customto afford 1.2 g (58%)

Sources & evidence

ORD record
ord-ef8074737c094ec5a2335129597a35c2
Source dataset
uspto-grants-2007_01
Patent number
US07157492B2

Reaction notes

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