O-(4-Nitrophenyl)hydroxylamine → (2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

HRID 1897855Notes

Reaction equation

HRID 1897855 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[CH2:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=1)C1C=CC=CC=1.[N+:24]([C:27]1[CH:32]=[CH:31][C:30](ON)=[CH:29][CH:28]=1)([O-:26])=[O:25]>Br.C(O)(=O)C>[CH2:18]([C:17]1[O:22][C:30]2[CH:31]=[CH:32][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][C:29]=2[C:16]=1[C:15](=[O:23])[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 15562106O-(4-Nitrophenyl)hydroxylamineHCID 667336971-(4-Benzyloxyphenyl)-heptane-1,3-dione

Product 1

HCID 11473234(2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanoneYield 59%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

1-(4-Benzyloxyphenyl)-heptane-1,3-dione (191 mg; see Example 1 (a)), was suspended in 1 ml HBr/acetic acid and O-4-nitrophenylhydroxylamine, 100 mg, was added. The mixture was stirred at room temperature for 6 h. After quenching with water and extraction to EtOAc followed by evaporation of the solvent, a crude material containing approximately 125 mg of the title compound was obtained. Yield ca. 59%.

Workup

  1. customAfter quenching with water and extraction to EtOAc
  2. customfollowed by evaporation of the solvent
  3. additiona crude material containing approximately 125 mg of the title compound
  4. customwas obtained

Sources & evidence

ORD record
ord-fd111c91ee794f7a801660e64ff52b8d
Source dataset
uspto-grants-2013_08
Patent number
US08519165B2

Reaction notes

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