Diethyl Oxalate → Ethyl 3-{2-[2-(dipropylamino)ethyl]-6-nitrophenyl}-2-oxopropanoate

HRID 1436862Notes

Reaction equation

HRID 1436862 reaction equation
[H-].[Na+].[C:3]([O:10][CH2:11][CH3:12])(=[O:9])[C:4]([O:6]CC)=O.[CH3:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:23][CH2:24][N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28]>C1COCC1>[CH2:11]([O:10][C:3](=[O:9])[C:4]([CH2:13][C:14]1[C:15]([CH2:23][CH2:24][N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[CH:16][CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])=[O:6])[CH3:12]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 13309224N,N-dipropyl-2-methyl-3-nitrophenylethanamine

Product 1

HCID 23322030Ethyl 3-{2-[2-(dipropylamino)ethyl]-6-nitrophenyl}-2-oxopropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (7.5 g) is added to Tetrahydrofuran (125 ml) at ambient temperature under Nitrogen atmosphere and stirred for 10-30 minutes. Diethyl oxalate (20 ml) is added to reaction mixture and at 25-45° C. and stirred the solution for 15 minutes. 2-Methyl-3-nitro-N, N-Di-n-propyl phenyl ethyl amine free base as generated above is added to reaction mixture and stirred slowly under nitrogen atmosphere at 25-30° C. for 36-72 hours. After completion of reaction THF is distilled out from the reaction mixture under vacuum at 35-70° C. and Ethyl acetate (250 ml) is added to reaction mass. Further, 3N HCl (approx. 30 ml) is added to adjust the pH of reaction mass to 7.5-8.0. Organic layer is separated out and dried over sodium sulphate. Ethyl acetate is distilled out to obtain Ethyl-6-(2-di-n-propylaminoethyl)-2-nitrophenylpyruvate.

Workup

  1. stirringstirred the solution for 15 minutes
  2. additionabove is added to reaction mixture
  3. stirringstirred slowly under nitrogen atmosphere at 25-30° C. for 36-72 hours
  4. distillationis distilled out from the reaction mixture under vacuum at 35-70° C.
  5. additionEthyl acetate (250 ml) is added to reaction mass
  6. additionFurther, 3N HCl (approx. 30 ml) is added
  7. customthe pH of reaction mass to 7.5-8.0
  8. customOrganic layer is separated out
  9. dry with materialdried over sodium sulphate
  10. distillationEthyl acetate is distilled out

Sources & evidence

ORD record
ord-1fc73bbaa7354fb490d8451560549722
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

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