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

HRID 1625191Notes

Reaction equation

HRID 1625191 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-8761b1c9861d4a9f9dbe1a6397c49bcd
Source dataset
uspto-grants-2014_07
Patent number
US08779201B2

Reaction notes

Loading…