HCID 10163434, compound → HCID 22238268, compound

HRID 1743224Notes

Reaction equation

HRID 1743224 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:34])=[C:16]([O:21][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][C:23]=4[N+:31]([O-])=O)[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11]2([CH3:36])[CH3:35])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H][H]>C(O)C.[C].[Pd]>[NH2:31][C:23]1[CH:24]=[C:25]([NH2:28])[CH:26]=[CH:27][C:22]=1[O:21][C:16]1[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]2[O:12][C:11]([CH3:35])([CH3:36])[CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=3)[C:14]=2[C:15]=1[CH3:34]

Participants

5

Reactant 2

HCID 10163434HCID 10163434, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22238268HCID 22238268, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

3-(4-Isopropylphenyl)-5-(2,4-dinitrophenyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran (800 mg, 1.63 mmol) and 10% palladium-carbon (hydrate) (80 mg) were dispersed in ethanol (40 mL), and the mixture was stirred in a hydrogen atmosphere at 60° C. for 4 hours. The reaction mixture, from which was removed the catalyst through filtration, was concentrated under reduced pressure to obtain 5-(2,4-diaminophenoxy)-3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran (710 mg). Acetyl chloride (0.26 mL, 3.63 mmol) was added to a solution of the thus-obtained compound (710 mg, 1.65 mmol) and triethylamine (290 mg, 1.70 mmol) in chloroform (30 mL) at 0° C., and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was poured into water (30 mL), and extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=1/5) to obtain the title compound (640 mg, yield 76%). This was amorphous.

Workup

  1. customThe reaction mixture, from which was removed the catalyst
  2. filtrationthrough filtration
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b63da9d162a447dc9897bde32746c8ee
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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