2-Ethylaniline → 3-(2-Ethylanilino)-4-(2-hydroxyanilino)-cyclobut-3-ene-1,2-dione

HRID 1743140Notes

Reaction equation

C(O[C:4]1[C:5](=[O:17])[C:6](=[O:16])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])C.[CH2:18]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22])[CH3:19]>CS(C)=O>[CH2:18]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:4]1[C:5](=[O:17])[C:6](=[O:16])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH3:19]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-ethoxy-4-(2-hydroxyanilino)-cyclobut-3-ene-1,2-dione (50 mg, 0.21 mmol) in DMSO (1.5 mL) was added 2-ethylaniline (0.024 mL, 0.21 mmol) and reaction was stirred at 110° C. overnight. Reaction was purified on HPLC (acetonitrile:water) and product was concentrated down. Solid was dried in vacuo. LC-MS (m/z) 309 (M+).

Workup

customReaction
customwas purified on HPLC (acetonitrile:water) and product
concentrationwas concentrated down
customSolid was dried in vacuo

Sources & evidence

ORD record: ord-8922f50bd2154cdd94a0a9244bc8e770
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008962B2

Reaction notes

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