N-methyl-2-pyrrolidone → Methyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate

HRID 2078038Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15](OCC)=[O:16])=[C:5]2[OH:20].Cl.[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH2:26].CN1CCCC1=O>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])([CH3:13])[C:7](=[O:14])[C:6]([C:15]([NH:26][CH2:25][C:24]([O:23][CH3:22])=[O:27])=[O:16])=[C:5]2[OH:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl 6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.224 g, 0.761 mmol), glycine methyl ester hydrochloride (0.115 g, 0.914 mmol, 99% Aldrich), 1-methyl-2-pyrrolidinone (1.5 mL), and TEA (0.32 mL, 2.28 mmol) was heated at 80° C. for 4 hours. The resulting mixture was cooled to room temperature and treated with water (10 mL) causing a white solid to precipitate. The product was collected by vacuum filtration and rinsed with water. MS m/e=338.0 (M+H)+.

Workup

temperatureThe resulting mixture was cooled to room temperature
customto precipitate
filtrationThe product was collected by vacuum filtration
washrinsed with water

Sources & evidence

ORD record: ord-967f0ddb60ee4ec99fbd7799b5d32ab7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

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