Pyridine → HCID 59211314, compound

HRID 2243450Notes

Reaction equation

HRID 2243450 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23]>C1(C)C=CC=CC=1>[CH3:20][C:21]([CH3:26])([CH3:25])[C:22]([O:18][C:17](=[O:19])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4661(4-Nitrophenyl)acetic acidHCID 62493Pivaloyl chloride

Product 1

HCID 59211314HCID 59211314, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyridine (14 g, 0.18 Mol) and 4-nitrophenylacetic acid (32 g, 0.18 Mol) were stirred in toluene (100 ml) whilst trimethylacetylchloride (21 g, 0.18 Mol) was added. The toluene was evaporated to yield 4-nitrophenylacetic-trimethylacetic anhydride. 3-Aminophenol (20 g, 0.18 Mol) was stirred in DMF (100 ml) and treated with the mixed anhydride and pyridine (14 g) in dimethylformamide (DMF) dropwise. The solution was diluted with water and the product isolated by filtration and dried (19 g, 39%).

Workup

  1. additionwas added
  2. customThe toluene was evaporated

Sources & evidence

ORD record
ord-730790bc5c5b4ef7a6e227ccbf7862ae
Source dataset
uspto-grants-2010_03
Patent number
US07674918B2

Reaction notes

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