O-Toluidine → 3-(2-Methylanilino)-4-(2-hydroxyanilino)-cyclobut-3-ene-1,2-dione

HRID 1743143Notes

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.[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>CS(C)=O>[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][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]

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-methylaniline (0.023 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) 295 (M+).

Workup

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

Sources & evidence

ORD record: ord-7b17f79fcad5463c82bb80e96f83fd89
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008962B2

Reaction notes

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