Hydrochloric Acid → HCID 21083236, compound

HRID 347634Notes

Reaction equation

HRID 347634 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl>CO.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21083245HCID 21083245, compound

Product 1

HCID 21083236HCID 21083236, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of the cyanobenzoyl benzaz pin from Example 1A (1.50 g, 5.43 mmol) in methanol (50 ml) were added concentrated hydrochloric acid (1.4 ml, 16.2 mmol) and 10% palladium-on-carbon (1.15 g). Hydrogen gas was bubbled through the mixture for 5 h at room temperature. The catalyst was removed by filtration through a pad of celite and the filtrate was evaporated in vacuo. The residue was partitioned between EtOAc and water. The aqueous layer was basified by addition of saturated sodium bicarbonate solution and extracted with dichloromethane (2 times). The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to give a white solid; yield 1.12 g (74%).

Workup

  1. customHydrogen gas was bubbled through the mixture for 5 h at room temperature
  2. customThe catalyst was removed by filtration through a pad of celite
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was partitioned between EtOAc and water
  5. additionThe aqueous layer was basified by addition of saturated sodium bicarbonate solution
  6. extractionextracted with dichloromethane (2 times)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a white solid

Sources & evidence

ORD record
ord-89d3f1d81801481fb78baf442d8fbb74
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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