18-Crown-6 → Methyl 2-[(2-nitrophenyl)amino]acetate

HRID 901939Notes

Reaction equation

HRID 901939 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(C(C)C)CC)(C)C.C1OCCOCCOCCOCCOCCOC1.[F-].[K+].F[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N+:44]([O-:46])=[O:45].S([O-])(O)(=O)=O.[K+]>C(#N)C.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N+:44]([O-:46])=[O:45]

Participants

9

Reactant 6

HCID 2855718-Crown-6HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 516920Potassium bisulfateHCID 522689Potassium Fluoride

Product 1

HCID 11252796Methyl 2-[(2-nitrophenyl)amino]acetateYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Glycine methyl ester hydrochloride (2.2 g, 18 mmol), diisopropylethylamine (2.9 g, 29 mmol), 18-crown-6 (370 mg, 1.4 mmol) and potassium fluoride (1.6 g, 28 mmol) were added to a solution of 1-fluoro-2-nitrobenzene (2 g, 14 mmol) in acetonitrile (150 ml). The mixture was heated at 80° C. for 48 h and cooled. 0.3N potassium hydrogen sulphate and ethyl acetate were added and the mixture separated. The organic phase was washed with water and brine, filtered through phase separation paper and reduced. Chromatography (15% EtOAc/85% 6080 petroleum ether) afforded N-(2-nitrophenyl)glycine methyl ester as a yellow solid (2.5 g, 85%).

Workup

  1. temperaturecooled
  2. customthe mixture separated
  3. washThe organic phase was washed with water and brine
  4. filtrationfiltered through phase separation paper

Sources & evidence

ORD record
ord-c66858a5313d4adc9bc7c03a88dfdf7a
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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