Toluene → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 2253354Notes

Reaction equation

HRID 2253354 reaction equation
C([NH:8][C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][C:15]([CH3:18])([CH3:17])[CH:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:13]=2[C:26]=1[CH3:27])C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)(C)C>[Pd].[C].O>[CH3:17][C:15]1([CH3:18])[CH:14]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[C:13]2[C:26]([CH3:27])=[C:9]([NH2:8])[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=2[O:16]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 3776IsopropanolHCID 10271436HCID 10271436, compound

Product 1

HCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amineYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N-benzyl-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (80 g), toluene (240 mL) and isopropanol (80 mL) was added 10% Pd-carbon (a product containing 50% water, 4 g), and the mixture was hydrogenated at 35° C. under atmospheric pressure. After completion of the reaction, the catalyst was filtered. Concentrated hydrochloric acid (19.2 mL) was added to the filtrate and the mixture was stirred at 10° C. or below for 1 hour. Precipitated crystals were filtered. The crystals were added to a mixture of methanol (560 mL) and water (80 mL) and the mixture was heated to 50° C. to dissolve the crystals. Then, 25% aqueous ammonia water was added dropwise to the solution to adjust to pH 8.5. Precipitated crystals were filtered to obtain the title compound (54.32 g, 88.6%).

Workup

  1. customwas hydrogenated at 35° C. under atmospheric pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered
  4. additionConcentrated hydrochloric acid (19.2 mL) was added to the filtrate
  5. customPrecipitated crystals
  6. filtrationwere filtered
  7. additionThe crystals were added to a mixture of methanol (560 mL) and water (80 mL)
  8. dissolutionto dissolve the crystals
  9. additionThen, 25% aqueous ammonia water was added dropwise to the solution
  10. customPrecipitated crystals
  11. filtrationwere filtered

Sources & evidence

ORD record
ord-316d46839f3e42caa377f8c8406edb69
Source dataset
uspto-grants-2008_01
Patent number
US07323577B2

Reaction notes

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