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

HRID 2176906Notes

Reaction equation

HRID 2176906 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-d9819b59497d46278559ad443ff7e996
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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