Dinitrofluorobenzene → Methyl N-(2,4-dinitrophenyl)glycinate

HRID 751023Notes

Reaction equation

HRID 751023 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH2:19].C([O-])([O-])=O.[K+].[K+]>CO>[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 272458Methyl N-(2,4-dinitrophenyl)glycinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-fluoro-2,4-dinitrobenzene (1) (15 g, 0.81 mmol), glycine methyl ester hydrochloride (11.5 g, 0.92 mmol), K2CO3 (22.3 g, 0.162 mmol) and methanol (300 mL) was heated at 60° C. for 30 minutes. After cooling in an ice bath, the resulting yellow precipitate was collected by filtration, washed with water and methanol and dried in vacuo. Yield 10.5 g (51%).

Workup

  1. temperatureAfter cooling in an ice bath
  2. filtrationthe resulting yellow precipitate was collected by filtration
  3. washwashed with water and methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c95a8d16b8e24ff396bc45ab5bd5da43
Source dataset
uspto-grants-2008_07
Patent number
US07405235B2

Reaction notes

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