3,4-Dimethoxy-5-nitrophenyl 2-thienyl ketone → 3,4-Dihydroxy-5-nitrophenyl 2-thienyl ketone

HRID 1781923Notes

Reaction equation

HRID 1781923 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([O:17]C)=[C:10]([O:19]C)[CH:9]=1)=[O:7]>Br.C(O)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([OH:17])=[C:10]([OH:19])[CH:9]=1)=[O:7]

Participants

4

Reactant 1

HCID 179776943,4-Dimethoxy-5-nitrophenyl 2-thienyl ketone

Product 1

HCID 179777183,4-Dihydroxy-5-nitrophenyl 2-thienyl ketone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Procedure

2 g of 3,4-dimethoxy-5-nitrophenyl 2-thienyl ketone are stirred at 100° for 8 hours in a mixture of 20 ml of 30-33 percent hydrobromic acid in glacial acetic acid and 20 ml of 48 percent aqueous hydrobromic acid. The reaction mixture is subsequently evaporated to dryness. The residue is taken up in ethyl acetate, washed with water, dried over sodium sulfate and filtered, and the filtrate is evaporated. After recrystallization from ethyl acetate/hexane there is obtained 3,4-dihydroxy-5-nitrophenyl 2-thienyl ketone of m.p. 155°-157°.

Workup

  1. customThe reaction mixture is subsequently evaporated to dryness
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customAfter recrystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-d4e18fa418d445f6af7e22b2933b4461
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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