Sodium Hydroxide → 4-Cyclopentylbenzene-1,2-diamine

HRID 1424223Notes

Reaction equation

HRID 1424223 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[C:8]([N+:16]([O-])=O)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>[Pd]>[CH:1]1([C:6]2[CH:7]=[C:8]([NH2:16])[C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86699135N-(4-cyclopentyl-2-nitrophenyl)acetamide

Product 1

HCID 866990854-Cyclopentylbenzene-1,2-diamineYield 50%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
90 °C

Procedure

A suspension of N-(4-cyclopentyl-2-nitrophenyl)acetamide (Preparation 86, 19.48 g, 78.46 mmol) in aqueous sodium hydroxide (6.0M, 100 mL, 600 mmol) was heated at 90° C. for 4 days. The reaction was allowed to cool and extracted with methylene chloride (3×). The organic layers were combined, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The resulting residue was suspended in methanol (300 mL) and treated with palladium (2 g, 20 mmol, 10% on carbon, Degussa type). The reaction mixture was hydrogenated at 40 psi for 5 hours before filtering through celite and concentrating in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (6.85 g, 50%) as a purple solid.

Workup

  1. temperatureto cool
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationbefore filtering through celite
  7. concentrationconcentrating in vacuo
  8. customThe residue was purified
  9. washeluting with a 0-100% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-982a0095b5f6425aa2be6f3be4760afe
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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