Ethyl 4-pyridinylcarbamate → 4-[N-(ethoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromide

HRID 1987844Notes

Reaction equation

HRID 1987844 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11])=[CH:3][CH:2]=1.[Br:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=1)=[O:16]>ClCCl>[Br-:13].[CH2:10]([O:9][C:8]([NH:7][C:4]1[CH:3]=[CH:2][N+:1]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=2)=[O:16])=[CH:6][CH:5]=1)=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 766500Ethyl 4-pyridinylcarbamateHCID 179579432-Bromo-1-(3-methoxy-4-nitrophenyl)-1-ethanone

Product 1

HCID 866075554-[N-(ethoxycarbonyl)amino]-1-[2-(3-methoxy-4-nitrophenyl)-2-oxoethyl]pyridinium bromideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared according to the same method as that described in Example 47, Step A by quaternization of 1.21 g (7.33 mmol) of ethyl 4-pyridinylcarbamate [described in J. Chem. Soc.; (1962), 2379-2381] with 2-bromo-1-(3-methoxy-4-nitrophenyl)-1-ethanone in dichloromethane. 3.24 g of a white precipitate are obtained.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-800eba0e6b92468e9119f313b664d63f
Source dataset
uspto-grants-2009_06
Patent number
US07553845B2

Reaction notes

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