Nitric Acid → [3-Hydroxy-4-methoxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitrophenyl]phenylmethanone

HRID 2075969Notes

Reaction equation

HRID 2075969 reaction equation
[OH:1][C:2]1[C:3]([O:22][CH3:23])=[CH:4][C:5]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[N+:24]([O-])([OH:26])=[O:25]>C(Cl)Cl>[OH:1][C:2]1[C:7]([N+:24]([O-:26])=[O:25])=[C:6]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[C:5]([C:16]2[N:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:4][C:3]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 136202003[5-Hydroxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl) phenyl]phenylmethanone

Product 1

HCID 136201962[3-Hydroxy-4-methoxy-6-(5-methyl-[1,2,4]oxadiazol-3-yl)-2-nitrophenyl]phenylmethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [5-hydroxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]phenylmethanone (reference example 21-1) (383 mg) and methylene chloride (10 mL) was added fuming nitric acid (68 μL) at room temperature, and the mixture was stirred for 20 minutes. The separated organic layer was washed with water, a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The residue was triturated with hexane:methylene chloride=4:1 to give the title compound (377 mg).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  3. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-86af14b3346540dab006c43f40d44800
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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