HCID 131717958, compound → HCID 131717957, compound

HRID 1109746Notes

Reaction equation

HRID 1109746 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=3)=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1>[OH-].[Na+]>[ClH:2].[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[CH:8][N:9]2[C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 131717958HCID 131717958, compound

Product 1

HCID 131717957HCID 131717957, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Compound 1a (10 g) was added to 100 ml of NaOH solution and the base was subsequently extracted with dichloromethane (2×50 ml). The organic phase was dried (anh. MgSO4) and the solvent evaporated. The remaining oil was dissolved in 100 ml of acetic acid and PtO2 (300 mg) was added. The mixture was hydrogenated in a Parr apparatus for 5 hrs at 3 atm. The catalyst was then filtered off, and the acetic acid was evaporated. Dil. NaOH solution (200 ml) and ethyl acetate (200 ml) were added to the remaining oil. The organic phase was separated, dried (anh. MgSO4) and ethyl acetate was evaporated leaving the crude title compound 3a as an oil. The hydrochloride salt crystallized from ethanol. Mp 268° C.

Workup

  1. extractionthe base was subsequently extracted with dichloromethane (2×50 ml)
  2. dry with materialThe organic phase was dried (anh. MgSO4)
  3. customthe solvent evaporated
  4. dissolutionThe remaining oil was dissolved in 100 ml of acetic acid
  5. additionPtO2 (300 mg) was added
  6. filtrationThe catalyst was then filtered off
  7. customthe acetic acid was evaporated
  8. additionDil. NaOH solution (200 ml) and ethyl acetate (200 ml) were added to the remaining oil
  9. customThe organic phase was separated
  10. dry with materialdried (anh. MgSO4) and ethyl acetate
  11. customwas evaporated

Sources & evidence

ORD record
ord-fee38ec0325c4e4dad593ffdcc715111
Source dataset
uspto-grants-1994_06
Patent number
US05322851

Reaction notes

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