Nitrogen → 6966-30-9

HRID 1109837Notes

Reaction equation

HRID 1109837 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:16])[C:10](=[N:14]O)[C:11]([OH:13])=[O:12])C.N(=C1C=CC=C[CH:20]1[C:21](CC(OCC)=O)=[O:22])O.[C:33](OC(=O)C)(=O)[CH3:34].[H][H].N#N>[Pd].C(O)(=O)C>[C:21]([NH:14][CH:10]([C:9](=[O:16])[C:4]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11]([O:13][CH2:33][CH3:34])=[O:12])(=[O:22])[CH3:20]

Participants

7

Reactant 4

HCID 947NitrogenHCID 7918Acetic AnhydrideHCID 178418361HCID 178418361, compoundHCID 178472165HCID 178472165, compound

Product 1

HCID 2272876966-30-9Yield 209.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

With stirring, a mixture of 221 g of ethyl 2-oximinobenzoylacetate (ethyl 2-oximino-3-oxo-3-phenylpropionate), 500 g of acetic anhydride, 50 g of glacial acetic acid and 20 g of a Pd/C catalyst (EF 101 R/W 51% H2O, sold by Degussa) is hydrogenated under normal pressure at 60° C. over 4 hours. The hydrogen uptake is 40 l. Afterwards the reactor is made inert with N2, flushed with nitrogen and the catalyst is removed by filtration. The filtrate is subsequently concentrated under reduced pressure on a rotary evaporator to give a residue (259.3 g), which is recrystallised from 200 ml of isopropanol/500 ml of petroleum ether.

Workup

  1. customflushed with nitrogen
  2. customthe catalyst is removed by filtration
  3. concentrationThe filtrate is subsequently concentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-e892b295ae4e4c9cb1ea0185f90691bf
Source dataset
uspto-grants-1994_06
Patent number
US05322964

Reaction notes

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