Sodium Acetate → HCID 18177413, compound

HRID 394691Notes

Reaction equation

HRID 394691 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:13]#[N:14].[C:15]([O-])(=[O:17])[CH3:16].[Na+]>C(OC(=O)C)(=O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]2[CH2:13][NH:14][C:15](=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 10679204HCID 10679204, compound

Product 1

HCID 18177413HCID 18177413, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

The nitrile obtained in Step A (200 mg; 1.05 mmol) is solubilised in the reactor of a Parr apparatus in 15 ml of acetic anhydride. Raney nickel (60 mg; 30% by weight) and also sodium acetate (1.5 eq; 1.58 mmol; 130 mg) are added. The reactor is placed under hydrogen pressure of 580 psi at 50° C. for 12 hours. When the reaction is complete, filtration over Celite and then rinsing with AcOEt are carried out. The product is purified by flash chromatography on silica gel (eluant: AcOEt (100%)). The white solid obtained is recrystallised from a pentane-ether mixture.

Workup

  1. customat 50° C.
  2. customfor 12 hours
  3. filtrationfiltration over Celite
  4. washrinsing with AcOEt
  5. customThe product is purified by flash chromatography on silica gel (eluant: AcOEt (100%))
  6. customThe white solid obtained
  7. customis recrystallised from a pentane-ether mixture

Sources & evidence

ORD record
ord-9155fefdb5cf4ad1b4df910f07a5b8bd
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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