9-amino-3,4-dihydroacridin-1(2H)-one → HCID 13756068, compound

HRID 1763011Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:17]N(C(N(C)C)C)C>FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[C:13](=[CH2:17])[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

Conditions

Temperature: 100 °C

Procedure

In 25ml of trifluoroacetic acid cooled in ice was dissolved 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one. To the solution was added dropwise 6.70ml (2.09 eq) of bisdimethylaminoethane over 5 minutes and thereafter the mixture was maintained at 90°100° C. for 5 hours during which the starting material was converted to a mixture of intermediate and exo-methylene products. The reaction mixture was poured into ice/NaOH to make it basic and the precipitate was extracted with several portions of 5:1 dichloromethane/MeOH. The combined extracts were evaporated to a residue. The residue was refluxed in toluene for 5 hours during which the intermediate was converted to the end product. The reaction mixture was evaporated to a residue which was purified by chromatography on silica gel (EtOAc) to yield about 2 g of a solid. This was recrystallized from dichloromethane/EtOAc to yield 1.79 g (34%) of product as a solid, melting point 119°-193° C.

Workup

additionwas converted to a mixture of intermediate and exo-methylene products
extractionthe precipitate was extracted with several portions of 5:1 dichloromethane/MeOH
customThe combined extracts were evaporated to a residue
temperatureThe residue was refluxed in toluene for 5 hours during which the intermediate
customThe reaction mixture was evaporated to a residue which
customwas purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record: ord-5c49e10cd73648f487c86c6ac06105a2
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835275

Reaction notes

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