3-Pyridinecarboxylic acid, 4-(acetylamino)phenyl ester → HCID 86717653, compound

HRID 2200843Notes

Reaction equation

HRID 2200843 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH:20]([N:23]([CH:29]([CH3:31])[CH3:30])[C:24](=[O:28])[O:25][CH2:26][I:27])([CH3:22])[CH3:21]>C(#N)C>[I-:27].[C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:1]([C:2]2[CH:3]=[N+:4]([CH2:26][O:25][C:24](=[O:28])[N:23]([CH:29]([CH3:31])[CH3:30])[CH:20]([CH3:22])[CH3:21])[CH:5]=[CH:6][CH:7]=2)=[O:8])=[CH:11][CH:12]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 32379893-Pyridinecarboxylic acid, 4-(acetylamino)phenyl esterHCID 86717655HCID 86717655, compound

Product 1

HCID 86717653HCID 86717653, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-acetamidophenyl nicotinate [297], (0.05 g, 1.95 mmol, 1.0 eq) in acetonitrile (4 ml) was added iodomethyl diisopropylcarbamate [6304] (0.055 g, 1.95 mmol, 1.0 eq). The resulting reaction mixture was stirred overnight at RT. The reaction was monitored by TLC. Acetonitrile was removed under vacuum and the resulting crude mixture was washed with diethyl ether (10 ml) to give pale yellow solid product 3-((4-acetamidophenoxy)carbonyl)-1-(((diisopropylcarbamoyl)oxy)methyl)pyridin-1-ium iodide [298] (0.086 g, 81%).

Workup

  1. customThe resulting reaction mixture
  2. customAcetonitrile was removed under vacuum
  3. washthe resulting crude mixture was washed with diethyl ether (10 ml)

Sources & evidence

ORD record
ord-76e628cd6eec487fac67b152e796e31d
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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