HCID 21220864, compound → HCID 21220910, compound

HRID 1584795Notes

Reaction equation

HRID 1584795 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-])=O)[CH:3]=1>C(O)C.[Pd]>[NH2:11][C:4]1[CH:3]=[C:2]([CH3:1])[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 21220864HCID 21220864, compound

Product 1

HCID 21220910HCID 21220910, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-methyl-5-nitro-2,3-dihydrobenzofuran (2 g) in ethanol (25 ml) was hydrogenated over palladium on carbon catalyst overnight. The catalyst was filtered off and the solvent removed in vacuo. The residue was partitioned between ether (30 ml) and hydrochloric acid (2M; 30 ml), the acid layer removed and the organic extracted with further acid. The combined acidic extracts were basified with 5M sodium hydroxide and extracted with ether (4×25 ml). The combined, dried (MgSO4), extracts were evaporated in vacuo to give the title compound as a brown solid (0.7 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed in vacuo
  3. customThe residue was partitioned between ether (30 ml) and hydrochloric acid (2M; 30 ml)
  4. customthe acid layer removed
  5. extractionthe organic extracted with further acid
  6. extractionextracted with ether (4×25 ml)
  7. dry with materialdried (MgSO4), extracts
  8. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-a5c749cefa794a19b0e23dee14d28cf4
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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