2,3-Dihydro-2,5-dimethyl-4-chloro-7-nitrobenzofuran → 7-Amino-2,3-dihydro-2,5-dimethyl-4-chlorobenzofuran

HRID 279897Notes

Reaction equation

HRID 279897 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2[C:7]([Cl:15])=[C:8]([CH3:14])[CH:9]=[C:10]([N+:11]([O-])=O)[C:4]=2[O:3]1.[H][H]>C1COCC1.[Pd]>[NH2:11][C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[C:7]([Cl:15])=[C:8]([CH3:14])[CH:9]=1

Participants

5

Reactant 2

HCID 135756772,3-Dihydro-2,5-dimethyl-4-chloro-7-nitrobenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 136308847-Amino-2,3-dihydro-2,5-dimethyl-4-chlorobenzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

51.0 g of 3C was dissolved in 600 ml of THF. The solution was divided in half, and each half was hydrogenated (40-50 psig hydrogen pressure) in the presence of 1 g of palladium-on-charcoal catalyst. The final combined reaction mixtures were filtered, the filtrates were combined, dried (MgSO4) and evaporated to dryness, to give 7-amino-2,3-dihydro-2,5-dimethyl-4-chlorobenzofuran (3D).

Workup

  1. customreaction mixtures
  2. filtrationwere filtered
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0304a65309b845ad8c043a8dab4a862a
Source dataset
uspto-grants-1986_05
Patent number
US04587259

Reaction notes

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