Sodium Acetate → HCID 20490860, compound

HRID 435118Notes

Reaction equation

HRID 435118 reaction equation
[C:1]([C:3]1[C:14]2=[C:15]3[N:10]([CH:11]([CH3:16])[CH2:12][CH2:13]2)[CH:9]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7](=[O:22])[C:6]3=[CH:5][CH:4]=1)#[N:2].[C:23]([O-])(=[O:25])[CH3:24].[Na+]>[Ni].C(OC(=O)C)(=O)C>[C:23]([NH:2][CH2:1][C:3]1[C:14]2=[C:15]3[N:10]([CH:11]([CH3:16])[CH2:12][CH2:13]2)[CH:9]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7](=[O:22])[C:6]3=[CH:5][CH:4]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 13156221HCID 13156221, compound

Product 1

HCID 20490860HCID 20490860, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.0 g (16.9 mmole) of ethyl 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate, 10 g of sodium acetate, 2 g of Raney nickel and 100 ml of acetic anhydride was stirred under hydrogen gas on a Paar apparatus at 50 psi and 50° C. for six hours. The catalyst was removed by filtration, and the filtrate was evaporated. The residue was dissolved in isopropyl alcohol and slowly crystallized to provide white crystals of ethyl 8-acetamidomethyl-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate. The structural assignment was supported by infrared spectral analysis.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in isopropyl alcohol
  4. customslowly crystallized

Sources & evidence

ORD record
ord-f33bdcd631dc43fd92415c2379036452
Source dataset
uspto-grants-1983_08
Patent number
US04400386

Reaction notes

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