HCID 131735472, compound → HCID 76847321, compound

HRID 633584Notes

Reaction equation

HRID 633584 reaction equation
[Cl:1][C:2]1[C:3]([CH:13]=[CH:14][N:15](C)C)=[C:4]([N+]([O-])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H][H]>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[NH:15][CH:14]=[CH:13][C:3]=12

Participants

5

Reactant 2

HCID 131735472HCID 131735472, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 76847321HCID 76847321, compoundYield 117.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 108C (12 g, 46.6 mmol) in ethyl acetate (150 mL) was added Raney-Ni (20.0 g, 4.66 mmol), and the reaction mixture was stirred for 20 hours at room temperature under 30 atm. hydrogen. The reaction mixture was filtered and rinsed with ethyl acetate. The filtrate was concentrated to a small volume, and the precipitates were collected by filtration and dried to provide the title compound (10 g, 93% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washrinsed with ethyl acetate
  3. concentrationThe filtrate was concentrated to a small volume
  4. filtrationthe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-dcae7173ec4c4e5c95afe1a6aa561342
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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