HCID 54515133, compound → HCID 20094757, compound

HRID 274091Notes

Reaction equation

HRID 274091 reaction equation
C1S[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=3)[CH2:6][CH:5]2[NH:15][C:16]([O:18][CH3:19])=[O:17])SC1>[Ni].C(O)C>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][CH:5]([NH:15][C:16]([O:18][CH3:19])=[O:17])[CH2:4]2

Participants

4

Reactant 1

HCID 54515133HCID 54515133, compound

Product 1

HCID 20094757HCID 20094757, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-methoxy-2-(methoxycarbonylamino)indan-1-one ethylene dithioacetal (0.12 g), Raney nickel (suspension in water; 5 ml), and ethanol (12 ml) was refluxed for 0.5 hour. The mixture was filtered and the catalyst was washed with hot ethanol. The filtrate and washings were combined and concentrated in vacuo. Purification of the residue by column chromatography on silica gel (eluent; chloroform) gave 5-methoxy-N-methoxycarbonylindan-2-amine (0.08 g).

Workup

  1. temperaturewas refluxed for 0.5 hour
  2. filtrationThe mixture was filtered
  3. washthe catalyst was washed with hot ethanol
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by column chromatography on silica gel (eluent; chloroform)

Sources & evidence

ORD record
ord-d12bdf6dcca84badb6c8a4b1cee90f60
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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