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 2260672Notes

Reaction equation

HRID 2260672 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-8bf07b1aece5432b96da74718e8cac17
Source dataset
uspto-grants-1995_12
Patent number
US05478844

Reaction notes

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