HCID 20279309, compound → HCID 131714244, compound

HRID 1248280Notes

Reaction equation

HRID 1248280 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]([CH3:17])[C:5]([O:6][CH:7]([C:10]2[NH:11][CH2:12][CH2:13][N:14]=2)[CH2:8]C)=[C:4]([CH3:18])[C:3]=1[N+:19]([O-])=O>C(O)C>[BrH:1].[NH:14]1[CH2:13][CH2:12][N:11]=[C:10]1[CH:7]([O:6][C:5]1[C:4]([CH3:18])=[C:3]([NH2:19])[CH:2]=[CH:16][C:15]=1[CH3:17])[CH3:8]

Participants

3

Reactant 1

HCID 20279309HCID 20279309, compound

Product 1

HCID 131714244HCID 131714244, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolCatalyst

Procedure

The title product of Example 6 (14.8 g) was hydrogenated in ethanol using 10% palladium on carbon as catalyst. Insolubles were removed by filtration and the filtrate was concentrated to an oil which solidified upon standing. The solid was triturated with diethyl ether and collected by filtration, giving the debrominated title compound (11.2 g) as a hydrated hydrobromide salt. Structure assignment was supported by nmr and infrared spectra and by elemental analysis.

Workup

  1. customInsolubles were removed by filtration
  2. concentrationthe filtrate was concentrated to an oil which
  3. customThe solid was triturated with diethyl ether
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4cb804cc2cee459e955e50603c32ff0d
Source dataset
uspto-grants-1985_06
Patent number
US04523020

Reaction notes

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