Hydrochloric Acid → HCID 44601040, compound

HRID 2381247Notes

Reaction equation

HRID 2381247 reaction equation
[C:1]([C:9]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18]([OH:23])[C:17]([O:24]C)=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>N1C=CC=CC=1>[C:1]([C:9]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18]([OH:23])[C:17]([OH:24])=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 58345558HCID 58345558, compound

Product 1

HCID 44601040HCID 44601040, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
77 °C

Procedure

To a mixture of ethyl 2-benzoyl-4-hydroxy-5-methoxy-3-nitrobenzoate (reference example 18-1) (806 mg) and ethyl acetate (10 mL) were added aluminum chloride (610 mg) and pyridine (0.889 mL). The mixture was stirred at 77° C. for 2 hours. After cooling to room temperature, 2 mol/L hydrochloric acid was added to the mixture. The separated organic layer was washed with brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with hexane:diethyl ether=4:1 to give the title compound (430 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe separated organic layer was washed with brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-3169c3cf614247aa993e19c15c553686
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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