2,5,7,8-TETRAMETHYL-2-(4-NITROPHENOXYMETHYL)-4-OXOCHROMAN-6-YL ACETATE → 2-[(4-Aminophenoxy)methyl]-2,5,7,8-tetramethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl acetate

HRID 1589705Notes

Reaction equation

HRID 1589705 reaction equation
[H][H].[C:3]([O:6][C:7]1[C:8]([CH3:32])=[C:9]2[C:14](=[C:15]([CH3:18])[C:16]=1[CH3:17])[O:13][C:12]([CH3:30])([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:11][C:10]2=[O:31])(=[O:5])[CH3:4]>[Pd].CO>[C:3]([O:6][C:7]1[C:8]([CH3:32])=[C:9]2[C:14](=[C:15]([CH3:18])[C:16]=1[CH3:17])[O:13][C:12]([CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)([CH3:30])[CH2:11][C:10]2=[O:31])(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 113504832,5,7,8-TETRAMETHYL-2-(4-NITROPHENOXYMETHYL)-4-OXOCHROMAN-6-YL ACETATEHCID 178418361HCID 178418361, compound

Product 1

HCID 136058312-[(4-Aminophenoxy)methyl]-2,5,7,8-tetramethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogen gas was passed for 2 hours through a mixture of 3.6 g of 6-acetoxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman-4-one, 1 g of 10% w/w palladium-on-carbon and 100 ml of methanol at room temperature under atmospheric pressure. The catalyst was then removed by filtration and the filtrate was condensed by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with a 2:1 by volume mixture of hexane and ethyl acetate, and the resulting crude product was recrystallized from acetone, to yield 6-acetoxy-2-(4-aminophenoxymethyl)-2,5,7,8-tetramethylchroman-4-one. Its melting point was 177°-178° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. washeluted with a 2:1 by volume mixture of hexane and ethyl acetate
  5. customthe resulting crude product was recrystallized from acetone

Sources & evidence

ORD record
ord-fd183d8f4d4a4ef299fac71ceb590344
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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