HCID 19092194, compound → HCID 68973917, compound

HRID 657540Notes

Reaction equation

HRID 657540 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])[CH2:8][CH:7]([CH2:14][C:15]#[N:16])[CH2:6]2.CO.N.[H][H]>CO.[Ni]>[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]([CH2:14][CH2:15][NH2:16])[CH2:8]2

Participants

6

Reactant 3

HCID 19092194HCID 19092194, compoundHCID 21705897Ammonia methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 68973917HCID 68973917, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5 g (2.3 mmoles) of (5,6-dimethoxy-2,3-dihydro-1H-inden-2-yl)acetonitrile are dissolved in 50 ml of methanol. 50 mL of a (7N) MeOH—NH3 solution and 0.5 g of Raney nickel are then added. Hydrogen is carried out for 4 days under a pressure of 5 bar, at 25° C. Filtration over Celite and evaporation of the filtrate to dryness are carried out. The residue is taken up in 50 mL of HCl (1N) and washed with ethyl acetate; the aqueous phase is then brought to pH=10 by adding NaOH (20%). Extraction with Et2O, washing with water, drying over MgSO4, filtration and evaporation to dryness are carried out. The expected product is obtained in the form an oil.

Workup

  1. filtrationFiltration
  2. customover Celite and evaporation of the filtrate to dryness
  3. washwashed with ethyl acetate
  4. additionby adding NaOH (20%)
  5. extractionExtraction with Et2O
  6. washwashing with water
  7. dry with materialdrying over MgSO4, filtration and evaporation to dryness

Sources & evidence

ORD record
ord-eece8a0253c34b5681999c0689915d61
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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