Diethyl Oxalate → HCID 117727660, compound

HRID 517621Notes

Reaction equation

HRID 517621 reaction equation
F[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][O-:16].[Na+].[C:18](OCC)(=[O:24])[C:19]([O:21][CH2:22]C)=[O:20]>CO>[CH3:22][O:21][C:19](=[O:20])[C:18](=[O:24])[CH2:8][C:6]1[CH:7]=[C:2]([O:16][CH3:15])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5207051-Fluoro-5-methyl-2,4-dinitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 117727660HCID 117727660, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-fluoro-5-methyl-2,4-dinitro-benzene (about 100.0 g, 0.5 mol) in methanol (about 1.5 L), sodium methoxide (about 108 g, 1.9 mol) and diethyl oxalate (about 136 mL, 1.0 mol) are added at a temperature of about −10° C. The resulting orange color suspension is slowly allowed to reach a temperature of about 15-20° C. in about 2 hours and continuous stirring is carried out at a temperature of about 15-20° C. over a period of about 32 hours. The reaction mixture is quenched with 1.5 N HCl (about 200 mL), the precipitated solid obtained is filtered and dried under vacuum to obtain the product [3-(5-methoxy-2,4-dinitro-phenyl)-2-oxo-propionic acid methyl ester] as pale yellow solid (about 125 g, 85%). 1H NMR (DMSO-d6, 300 MHz): 3.84 & 3.87 (2s, 3H), 4.02 & 4.04 (2s, 3H), 8.63 & 10.93 (s & bs, 2H), 7.56 & 8.07 (2s, 1H), 8.63 & 8.75 (2s, 1H); LC-MS (ESI): 297.0 (M-H).

Workup

  1. additionare added at a temperature of about −10° C
  2. customa temperature of about 15-20° C.
  3. customin about 2 hours
  4. customThe reaction mixture is quenched with 1.5 N HCl (about 200 mL)
  5. customthe precipitated solid obtained
  6. filtrationis filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-711bfaf7242d468cae2797c4e462f0bf
Source dataset
uspto-grants-2015_08
Patent number
US09115128B2

Reaction notes

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