HCID 58566315, compound → HCID 58566656, compound

HRID 1876406Notes

Reaction equation

HRID 1876406 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[C:8]([N+:16]([O-])=O)[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[O:3]1.[H][H]>C(O)C.[Pd]>[NH2:16][C:8]1[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]2[O:3][C:2]([CH3:19])([CH3:1])[CH2:6][C:5]=2[CH:7]=1

Participants

5

Reactant 2

HCID 58566315HCID 58566315, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58566656HCID 58566656, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution ethyl 2,2-dimethyl-5-nitro-2,3-dihydrobenzofuran-7-carboxylate (674) (1.02 g, 3.84 mmol) in ethanol (40 mL) was added Pd/C (100 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight at room temperature, filtered through a pad of celite and concentrated in vacuo to give ethyl 5-amino-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (675) (899 mg, 99%)

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ccb580cb1044900b8ed5e55cb14f61f
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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