Ethyl cyanoacetate → HCID 15037319, compound

HRID 1886393Notes

Reaction equation

HRID 1886393 reaction equation
O=C1CCCNC([C:9]([O:11][CH2:12][CH3:13])=[O:10])C1.[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15].S1[CH:26]=[CH:25][CH:24]=[CH:23]1.[H][H].[CH2:29]([N:31](CC)[CH2:32]C)C>CO.[Pd]>[C:14]([CH:16]([CH:24]1[CH2:25][CH2:26][CH2:32][N:31]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:29][CH2:23]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15]

Participants

8

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 8030ThiopheneHCID 8471TriethylamineHCID 68866648HCID 68866648, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15037319HCID 15037319, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 56 parts of ethyl hexahydro-4-oxo-1H-azepinecarboxylate, 40 parts of ethyl 2-cyanoacetate, 60 parts of N,N-diethylethanamine, 400 parts of methanol and 3 parts of thiophene in methanol 4% was hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 84.6 parts (99.8%) of ethyl α-cyano-1-(ethoxycarbonyl)hexahydro-1H-azepine-4-acetate as a residue (int. 24).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c125e561350d493aa8fab9d316bf0c32
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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