Diethyl squarate → 3-Ethoxy-4-(4-hydroxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-5-ylamino)cyclobut-3-ene-1,2-dione

HRID 1528171Notes

Reaction equation

[NH2:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH2:6][N:7]([CH3:13])[C:8]2=[O:12])=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17]1[C:18](=O)[C:19](=[O:24])[C:20]=1[O:21]CC)[CH3:15]>C(O)C>[CH2:14]([O:16][C:17]1[C:20](=[O:21])[C:19](=[O:24])[C:18]=1[NH:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][N:7]([CH3:13])[C:8]2=[O:12])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.19 g (1.07 mmol) of 6-amino-7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one and 0.80 g (4.70 mmol) of 3,4-diethoxycyclobut-3-ene-1,2-dione in 10 ml of ethanol was heated at 60° C. for 24 hours. The reaction medium was concentrated and was taken up with diethyl ether with stirring (formation of a precipitate). The solid obtained was filtered off, washed twice with diethyl ether and dried. 235 mg of product were obtained. Yield=73%.

Workup

concentrationThe reaction medium was concentrated
customThe solid obtained
filtrationwas filtered off
washwashed twice with diethyl ether
customdried

Sources & evidence

ORD record: ord-8187bfd8875f46f7a713dd319d1f462d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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