4-hydroxy-3-methoxy-N-[1-oxo-2-phenylmethylidene-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide → 4-Hydroxy-3-methoxy-n-[1-oxo-2-phenylmethyl-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide

HRID 7085Notes

Reaction equation

HRID 7085 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][C:18](=[CH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:19]3=[O:22])=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:30][CH3:31]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH:18]([CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:19]3=[O:22])=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:30][CH3:31]

Participants

4

Reactant 1

HCID 696639674-hydroxy-3-methoxy-N-[1-oxo-2-phenylmethylidene-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide

Product 1

HCID 220195914-Hydroxy-3-methoxy-n-[1-oxo-2-phenylmethyl-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamideYield 69.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 248 (500 mg) is dissolved in ethyl acetate (20 ml), and thereto is added 10% palladium on carbon (50 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (350 mg).

Workup

  1. customis subjected to catalytic hydrogenation at 25° C
  2. customThe catalyst is removed by filtration
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d8739e16661d40b6a3416da0f3f2f41c
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Reaction notes

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