4-Nitrobenzoic Acid → HCID 2763952, compound

HRID 2110995Notes

Reaction equation

HRID 2110995 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([O:17][CH3:18])(=[O:16])[C:14]#[CH:15].CN1CCOCC1>C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:15]=[CH:14][C:13]([O:17][CH3:18])=[O:16])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 79724-MethylmorpholineHCID 13536Methyl propiolate

Product 1

HCID 2763952HCID 2763952, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

4-Nitrobenzoic acid (10 g, 59.8 mmol) and methyl propargylate (5.5 g, 65.8 mmol) were dissolved in acetonitrile (100 ml), N-methylmorpholine (3 g, 30 mmol) was added, and the mixture was stirred overnight at 40° C. The reaction mixture was concentrated under reduced pressure, and the residue was washed with ether to give the title compound (12.6 g, 50.2 mmol, 83.9%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-8aba284b0eb94eb689cc3292e47d3804
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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