Hydrochloric Acid → [3,4-Dihydroxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-phenyl]phenylmethanone

HRID 2075971Notes

Reaction equation

HRID 2075971 reaction equation
[OH:1][C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[C:4]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:5]([C:10]2[N:14]=[C:13]([CH3:15])[O:12][N:11]=2)=[CH:6][C:7]=1[O:8]C.C(OCC)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>N1C=CC=CC=1>[OH:1][C:2]1[C:3]([N+:24]([O-:26])=[O:25])=[C:4]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:5]([C:10]2[N:14]=[C:13]([CH3:15])[O:12][N:11]=2)=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 136201962[3-Hydroxy-4-methoxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitrophenyl]phenylmethanone

Product 1

HCID 135911995[3,4-Dihydroxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitro-phenyl]phenylmethanoneYield 87.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of [3-hydroxy-4-methoxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitrophenyl]phenylmethanone (reference example 22-1) (377 mg) and ethyl acetate (10.6 mL) were added aluminum chloride (361 mg) and pyridine (0.387 mL). The mixture was refluxed for 2.5 hours. After cooling to room temperature, 1 mol/L hydrochloric acid was added to the mixture. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with hexane:methylene chloride=4:1 to give the title compound (317 mg) as an amorphous.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. washThe separated organic layer was washed with brine
  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-b598322d54b941f991a796408cd17e8a
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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