Diethyl methyl(4-nitrophenyl)propanedioate → HCID 12370795, compound

HRID 1896269Notes

Reaction equation

HRID 1896269 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]>CCO>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:2]([CH3:1])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 12380744Diethyl methyl(4-nitrophenyl)propanedioate

Product 1

HCID 12370795HCID 12370795, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (30.60 g, 135.6 mmol) was added to a solution of diethyl 2-methyl-2-(4-nitrophenyl)malonate (8.00 g, 27.1 mmol) in EtOH (100 ml) and stirred at reflux for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken in water and basified with triethyl amine to adjust a pH˜8. The precipitated solid was filtered and washed with ethyl acetate. The separated organic layer from the filtrate was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 6.0 g (83%) of diethyl 2-(4-aminophenyl)-2-methylmalonate as brown oil.

Workup

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe precipitated solid was filtered
  4. washwashed with ethyl acetate
  5. washThe separated organic layer from the filtrate was washed with water, brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7063fd031a3140019bd81b47b10d4fbc
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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