Water → Diethyl 2-Amino-2-(4-Octylphenethyl)malonate

HRID 617876Notes

Reaction equation

HRID 617876 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:18][CH:17]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])[CH3:4].[N+:30](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O.O>CN(C)C=O>[NH2:30][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:21]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 21849265Ethyl 2-Ethoxycarbonyl-4-(4-octylphenyl)butyrate

Product 1

HCID 21849165Diethyl 2-Amino-2-(4-Octylphenethyl)malonateYield 133.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (0.38 g) was suspended in dry dimethyl-formamide (30 ml) and ethyl 2-ethoxycarbonyl-4-(4-octylphenyl)-butyrate (3.0 g) was added thereto. The mixture was stirred at room temperature for 2 hours. O-(2,4-Dinitrophenyl)hydroxyl-amine (1.14 g) was added thereto and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into cool water and extracted with toluene. The extract was washed with aqueous sodium chloride and dried over magnesium sulfate. The solvent was distilled away under reduced pressure to give 3 g of the subject compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. additionThe reaction mixture was poured
  3. extractionextracted with toluene
  4. washThe extract was washed with aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b7b0dae6e6ba4da2ab840cf29a0d3279
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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