Ethylamine → HCID 67201187, compound

HRID 546275Notes

Reaction equation

Br[CH:2]([C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([O:12]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:19]([NH2:21])[CH3:20]>O1CCCC1>[CH2:19]([N:21]1[C:10](=[O:12])[C:9]2[C:8](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:20]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of ethyl 2-[1-bromo-2-(ethyloxy)-2-oxoethyl]benzoate (2.11 g, 6.7 mmol) in anhydrous tetrahydrofuran (200 ml) was treated with a 2M solution of ethylamine in tetrahydrofuran (8 ml, 16 mmol) and stirred at 20° C. for 48 hrs. The tetrahydrofuran was removed by evaporation and then the residue was taken up in ethyl acetate (150 ml) and water (150 ml). The aqueous phase was separated and extracted with more ethyl acetate (100 ml) and then the combined organic fractions was washed with saturated aqueous sodium chloride solution (150 ml) and then dried over magnesium sulphate and evaporated to give a yellow oil. The oil was purified by automated flash silica-gel column chromatography (using a Biotage SP4), eluting with 10-50% gradient of ethyl acetate in hexane, to give ethyl 2-ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylate (1.4 g) as a colourless oil which solidified on standing and was used in the next step without further purification.

Workup

customThe tetrahydrofuran was removed by evaporation
customThe aqueous phase was separated
extractionextracted with more ethyl acetate (100 ml)
washthe combined organic fractions was washed with saturated aqueous sodium chloride solution (150 ml)
dry with materialdried over magnesium sulphate
customevaporated
customto give a yellow oil
customThe oil was purified by automated flash silica-gel column chromatography (
washeluting with 10-50% gradient of ethyl acetate in hexane

Sources & evidence

ORD record: ord-6b8ea387208b4997b53d96995a9fea95
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935832B2

Reaction notes

Loading…