HCID 71090169, compound → HCID 86715698, compound

HRID 716820Notes

Reaction equation

HRID 716820 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:21])[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 71090169HCID 71090169, compound2×

Product 1

HCID 86715698HCID 86715698, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-Dimethyl-6-(4-nitrophenoxy)-1,3-dihydro-2-benzofuran (Intermediate 69, 280 mg, 0.98 mmol) was dissolved in ethanol (5 ml), 5% w/w Pd/C was added and the reaction mixture was stirred for 4 hours under hydrogen atmosphere (2 bar). The catalyst was filtered off and the solvent evaporated to dryness to afford a pale yellow solid, which was purified by re-slurry in Et2O, to afford the title compound (80 mg) as off-white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated to dryness
  3. customto afford a pale yellow solid, which
  4. customwas purified by re-slurry in Et2O

Sources & evidence

ORD record
ord-bbd744aed378450a9305d04c1599214e
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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