Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 58683750, compound

HRID 1991064Notes

Reaction equation

HRID 1991064 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[CH:14]=O)[N:10]=[CH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:16][O:17][C:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19]>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18](=[O:19])/[CH:20]=[CH:14]/[C:13]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 58683726HCID 58683726, compound

Product 1

HCID 58683750HCID 58683750, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Nitroquinolin-7-carbaldehyde (920 mg; 4.55 mmol) in toluene (46 ml) and (methoxycarbonylmethylen)triphenylphosphoran (1.67 g; 5.0 mmol) were refluxed for 1 h. The title compound crystallised upon cooling and was filtered off. Recrystallisation from hot EtOAc (250 ml) gave pure title compound (700 mg). The mother liquor was purified via chromatography (SiO2; acetone/hexanes 30/70) to yield a further batch of pure title compound (300 mg). Total yield: 1 g; 85%.

Workup

  1. customThe title compound crystallised
  2. temperatureupon cooling
  3. filtrationwas filtered off
  4. customRecrystallisation from hot EtOAc (250 ml)

Sources & evidence

ORD record
ord-1248a96ce6c24adfb1947f88202d6534
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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