Chloroform → 9,10-Dihydro-7-methyl-9-oxo-3-acridinecarboxylic Acid

HRID 970322Notes

Reaction equation

[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:3][CH:2]=1.C(Cl)(Cl)Cl>CO.O.O1CCOCC1>[CH3:20][C:1]1[CH:2]=[C:3]2[C:4]([NH:7][C:8]3[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:9]=3[C:10]2=[O:12])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a round bottom flask equipped with a condenser was added compound 138A (2.0 g), polyphosphoric acid (15 g) and CHCl3 (50 mL), and the mixture was heated to 100° C. for 18 h. LC/MS indicated that the reaction was complete. The reaction mixture was cooled to room temperature, diluted with MeOH (25 mL), and H2O (50 mL) was added. The resulting mixture was filtered through a medium porosity fritted funnel, washed with MeOH:1% Et3N in H2O (1:1, 30 mL) two times, and dried in air to give a yellow paste which was then dispersed in dioxane (10 mL) with sonication and dried over lyophlyzer to give compound 138B as a yellow solid (2.0 g). HPLC retention time: 2.76 min., condition A. M+: 254.

Workup

customTo a round bottom flask equipped with a condenser
temperatureThe reaction mixture was cooled to room temperature
additionwas added
filtrationThe resulting mixture was filtered through a medium porosity fritted funnel
washwashed with MeOH
dry with material1% Et3N in H2O (1:1, 30 mL) two times, and dried in air
customto give a yellow paste which
customdried over lyophlyzer

Sources & evidence

ORD record: ord-97a86e408d3a4c4aa1fcf812f22f0b64
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312209B2

Reaction notes

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