2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran → 5-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran

HRID 234251Notes

Reaction equation

HRID 234251 reaction equation
[CH3:1][C:2]1([CH3:23])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]2[C:13]([CH3:22])=[C:14]([N+:19]([O-])=O)[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]=2[O:3]1>C(O)C.[C].[Pd]>[NH2:19][C:14]1[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]2[O:3][C:2]([CH3:23])([CH3:1])[CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:5]=2[C:13]=1[CH3:22]

Participants

4

Reactant 1

HCID 106628262,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran

Product 1

HCID 105407985-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuranYield 73.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

2,2,4,6,7-Pentamethyl-5-nitro-3-phenyl-2,3-dihydrobenzofuran (2.0 g, 6.4 mmol) was dissolved in ethanol (15 ml) and the solution was subjected to catalytic reduction using 5% palladium carbon (2.0 g) as a catalyst. After the catalyst was filtered off, the filtrate was concentrated. The residue was purified by column chromatography on silica gel (isopropyl ether) and then crystallized from hexane to obtain the desired compound (1.33 g, yield: 73.6%), m.p. 131°-132° C.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (isopropyl ether)
  4. customcrystallized from hexane

Sources & evidence

ORD record
ord-25f3ae4eb8ef4b8bb3714202cb4a2c20
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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