Water → Diethyl methyl-(4-amino)benzylmalonate

HRID 2176910Notes

Reaction equation

HRID 2176910 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][C:9]([CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.C(OCC)(=O)C.C(N(CC)CC)C>CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]([CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54496963Diethyl 2-(4-nitrobenzyl)-2-methylmalonate

Product 1

HCID 54055855Diethyl methyl-(4-amino)benzylmalonateYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (4.39 g, 19.4 mmol) was added to a solution of diethyl 2-(4-nitrobenzyl)-2-methylmalonate (3.00 g, 9.70 mmol) in EtOH (30 ml) and stirred at reflux for 3 h. Water and ethyl acetate were added and the solution was basified with triethyl amine adjusted an pH˜9. The salts were filtered and washed with ethyl acetate. The organic layer was separated from the filtrate and washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2.20 g (81.4%) of diethyl 2-(4-aminobenzyl)-2-methylmalonate as brown oil.

Workup

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

Sources & evidence

ORD record
ord-a6b7108b220e4b9797cd5cd64c95f198
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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