Trifluoroacetic anhydride → 6-Methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one

HRID 478694Notes

Reaction equation

CO[C:3]1[CH:4]=[CH:5][C:6]([NH:15][C:16]2[C:17]([C:26]([OH:28])=O)=[CH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH:9]=[CH:8]2.FC(F)(F)[C:31](OC(=O)C(F)(F)F)=[O:32]>ClCCl>[CH3:31][O:32][C:4]1[CH:3]=[C:12]2[O:11][C:10]([CH3:13])([CH3:14])[CH:9]=[CH:8][C:7]2=[C:6]2[C:5]=1[C:26](=[O:28])[C:17]1[CH:18]=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]3=[CH:25][C:16]=1[NH:15]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution containing 1.94 mmol of the compound obtained in Step 1 in 20 ml of anhydrous dichloromethane, maintained at 0° C. under argon, there are added 9.71 mmol of trifluoroacetic anhydride. After reacting for 3 days at ambient temperature, the reaction mixture is concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and aqueous NaHCO3 solution. After extraction with dichloromethane, the combined organic phases are treated in conventional manner. Chromatography of the residue over silica gel (dichloromethane) allows the expected product to be isolated, the latter being subsequently recrystallised from ethyl ether.

Workup

concentrationthe reaction mixture is concentrated under reduced pressure
additionThe residue is taken up in a mixture of dichloromethane and aqueous NaHCO3 solution
extractionAfter extraction with dichloromethane
additionthe combined organic phases are treated in conventional manner
customto be isolated
customthe latter being subsequently recrystallised from ethyl ether

Sources & evidence

ORD record: ord-11340ce2575e43b9846f2b35f9851493
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642248B2

Reaction notes

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