Pyridinium hydrochloride → HCID 69673855, compound

HRID 1751390Notes

Reaction equation

HRID 1751390 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15]C)=[CH:12][CH:13]=3)[O:8][CH2:7][C:6]=2[CH:17]=1.Cl.[NH+]1C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=3)[O:8][CH2:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 69672702HCID 69672702, compound

Product 1

HCID 69673855HCID 69673855, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-chloro-3-methoxy-6H-benzo[c]chromene (670 mg, 2.7 mmol) and piridinium hydrochloride (3.16 g, 27.3 mmol) were heated to 185° C. for 2.5 hours. After cooling to room temperature, the reaction was diluted with water extracted into ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield 8-chloro-6H-benzo[c]chromen-3-ol (523 mg, 82%)

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organics were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a5758de487a24645a8bbd825f3192f55
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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