Nitrogen → HCID 11299024, compound

HRID 1485352Notes

Reaction equation

HRID 1485352 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].[CH3:16][Si](C=[N+]=[N-])(C)C.N#N>CO.C1C=CC=CC=1>[CH3:16][O:4][C:3](=[O:5])[C:2]([CH3:1])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH3:6]

Participants

5

Reactant 3

HCID 947NitrogenHCID 167693TrimethylsilyldiazomethaneHCID 7818982-Methyl-2-(4-nitrophenyl)propanoic acid

Product 1

HCID 11299024HCID 11299024, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a solution of 2-methyl-2-(4-nitrophenyl)-propionic acid (1.0014 g, 4.76 mmol) in 10% MeOH/benzene (20 mL) was added dropwise (trimethylsilyl)-diazomethane (2.0 M in hexanes, 3.5 mL, 7.0 mmol). The reaction mixture was stirred at rt until evolution of N2 ceased (<5 min) and then concentrated. The crude residue was purified (FCC) to give the title compound (937.6 mg, 88%).

Workup

  1. custom(<5 min)
  2. concentrationconcentrated
  3. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-d6d8068c850e43a4bb19b33410b48205
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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