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Acetamidomalonic acid diethyl ester → Diethyl-alpha-methyl-2-naphthylacetamidomalonate

HRID 1293508
Notes
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Reaction equation

HRID 1293508 reaction equation
BrC([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)C.[C:14]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])[CH3:15].[CH3:29]C[O-].[Na+]>C(O)C>[CH2:22]([O:21][C:19](=[O:20])[C:18]([NH:17][C:14](=[O:16])[CH2:15][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 186782542-(1-Bromoethyl)naphthalene

Product 1

HCID 86601358Diethyl-alpha-methyl-2-naphthylacetamidomalonateYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

2-(1-Bromoethyl)-naphthalene (105 g, 446 mmol) in anhydrous ethanol (150 mL) was added to a stirred solution of diethyl acetamidomalonate (97.6 g, 450 mmol) previously reacted with sodium ethylate (sodium metal 10.3 g, 448 mmol) in anhydrous ethanol (400 mL). The reaction mixture was stirred at 40° C. overnight. After removal of two-thirds of the solvent in vacuo and keeping the mixture in the refrigerator overnight, the precipitated product and NaBr crystals were collected by filtration. The solid was washed with cold ethanol and distilled water (to eliminate NaBr), yielding 112 g (67%) of diethyl-α-methyl-2-naphthylacetamidomalonate as white crystals: mp 148-150° C.; C21H25NO5 MS: 371,44.

Workup

  1. customAfter removal of two-thirds of the solvent in vacuo
  2. customin the refrigerator overnight
  3. filtrationthe precipitated product and NaBr crystals were collected by filtration
  4. washThe solid was washed with cold ethanol
  5. distillationdistilled water (to eliminate NaBr)

Sources & evidence

ORD record
ord-9f7fedbc95f6478f97442db2e9e0dbad
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes