Sulfuric Acid → 5,6-dimethoxy-2,3-dihydro-1H-inden-2-amine

HRID 1952969Notes

Reaction equation

HRID 1952969 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[C:7](=[N:15]O)[CH2:6]2.S(=O)(=O)(O)O>C(O)(=O)C.O.[Pd]>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH:7]([NH2:15])[CH2:8]2

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 67540042-(Hydroxyimino)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 110416235,6-dimethoxy-2,3-dihydro-1H-inden-2-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 5,6-dimethoxy-2-hydroxyimino-1-indanone (0.27 moles, 6 g) in glacial acetic acid (500 ml) is added with 96% sulfuric acid (3.3 ml) and 10% Pd/C (1.5 g). The mixture is hydrogenated in a Parr apparatus (r.t., 35 psi). When the hydrogen absorption ceases, the catalyst is filtered off through celite, washing with methanol (70 ml). The solution is evaporated to dryness, to obtain a white solid which is dissolved in water, then extracted with ethyl acetate (2×70 ml). The aqueous solution is alkalinized with a 1M sodium hydroxide solution to pH=8-8.5. The product is extracted with methylene chloride (2×70 ml). The organic solution is dried over sodium sulfate and evaporated under vacuum to obtain the solid product. Yield: 4.6 g (88.5%)

Workup

  1. customis hydrogenated in a Parr apparatus (r.t., 35 psi)
  2. customWhen the hydrogen absorption ceases
  3. filtrationthe catalyst is filtered off through celite
  4. washwashing with methanol (70 ml)
  5. customThe solution is evaporated to dryness
  6. customto obtain a white solid which
  7. extractionextracted with ethyl acetate (2×70 ml)
  8. extractionThe product is extracted with methylene chloride (2×70 ml)
  9. dry with materialThe organic solution is dried over sodium sulfate
  10. customevaporated under vacuum
  11. customto obtain the solid product

Sources & evidence

ORD record
ord-b7046c95c1b340e4927078671ff3c56d
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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