90060-20-1 → HCID 19352272, compound

HRID 726889Notes

Reaction equation

HRID 726889 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[C:7]1=O)=[O:4].Cl.OC1C(O)=CC=C2C=1CCC(NC)C2>CO.[Pd]>[CH3:1][O:2][C:3]([NH:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 691848290060-20-1HCID 19352269HCID 19352269, compound

Product 1

HCID 19352272HCID 19352272, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

50 g of 2-methoxycarbonylamino-5,6-dimethoxy-1-tetralone are dissolved in 500 ml of methanol in a 1000 ml flask, with stirring, 20 g of 5% Pd/C are added, then the whole is placed into an autoclave (Hastelloy) under hydrogen atmosphere at 80° C. and a pressure of 25 atm. for about 6 hours with stirring, after that the mixture is left to cool to about 30° C. in autoclave. The mixture is filtered through Celite and the filtrate is evaporated to dryness under vacuum. The resulting white solid is triturated in 400 ml of n-hexane at 60° C., then is left to cool to about 30° C. with stirring, filtered and dried under vacuum at 60 ° C., to obtain a whitish solid. Yield: 40.6 g, 85.5% (moles), 81.2% (weight); T.L.C. Methylene chloride 95-Methanol 5; Rf=0.76; M.p.=108.7°-111.4 ° C.

Workup

  1. stirringa pressure of 25 atm. for about 6 hours with stirring
  2. waitafter that the mixture is left
  3. filtrationThe mixture is filtered through Celite
  4. customthe filtrate is evaporated to dryness under vacuum
  5. customThe resulting white solid is triturated in 400 ml of n-hexane at 60° C.
  6. waitis left
  7. temperatureto cool to about 30° C.
  8. stirringwith stirring
  9. filtrationfiltered
  10. customdried under vacuum at 60 ° C.
  11. customto obtain a whitish solid

Sources & evidence

ORD record
ord-060cf77c801f4c2b9ab5e12da8b48f29
Source dataset
uspto-grants-1998_01
Patent number
US05710336

Reaction notes

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