Water → ethyl (Z)-2-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)acrylate

HRID 390588Notes

Reaction equation

HRID 390588 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH2:23]([O:25]/[C:26](=[CH:32]\[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([NH:45][CH3:46])[N:40]=2)=[CH:35][CH:34]=1)/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:24].O>ClCCl>[CH2:23]([O:25]/[C:26](=[CH:32]\[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([N:45]([CH3:46])[C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[N:40]=2)=[CH:35][CH:34]=1)/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 86626072ethyl (Z)-2-ethoxy-3-[4-(6-methylaminopyrid-2-yl)phenyl]acrylate

Product 1

HCID 86626074ethyl (Z)-2-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)acrylateYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.55 g (2.75 mmol) of 4-nitrophenyl chloroformate and then 0.48 mL (2.75 mmol) of diisopropylethylamine are added to a solution of 0.6 g (1.84 mmol) of ethyl (Z)-2-ethoxy-3-[4-(6-methylaminopyrid-2-yl)phenyl]acrylate in 15 mL of dichloromethane. The reaction mixture is stirred for 1 hour 30 minutes at room temperature. The reaction is worked up by addition of 10 mL of water and extraction with dichloromethane. The organic phases are combined and then dried over magnesium sulfate, filtered and the solvent is evaporated off. 1 g (100%) of ethyl (Z)-2-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)acrylate is obtained in the form of a yellow oil.

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationfiltered
  3. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-5f85bd31d6b34cd89c7066ee24110862
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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