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

HRID 1293508Notes

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]

Participants

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

customAfter removal of two-thirds of the solvent in vacuo
customin the refrigerator overnight
filtrationthe precipitated product and NaBr crystals were collected by filtration
washThe solid was washed with cold ethanol
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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