Reaction #54743

ord-8b3942a0c8564b7ba8398b09d967d53d

Reaction equation

CN(C)CCOc1ccc2c(=O)c3ccccc3n(Cc3ccccc3)c2c1
3-(2-dimethylaminoethoxy)-10-benzyl-9(10H)-acridinone
O=c1c2ccccc2[nH]c2cc(Cl)ccc12
3-chloro-9(10H)-acridinone
BrCc1ccccc1
benzyl bromide
[H-].[Na+]
sodium hydride
→
O=c1c2ccccc2n(Cc2ccccc2)c2cc(Cl)ccc12
3-chloro-10-benzyl-9(10H)-acridinone

Reactants

CN(C)CCOc1ccc2c(=O)c3ccccc3n(Cc3ccccc3)c2c1
3-(2-dimethylaminoethoxy)-10-benzyl-9(10H)-acridinone
—
IV
O=c1c2ccccc2[nH]c2cc(Cl)ccc12
3-chloro-9(10H)-acridinone
BrCc1ccccc1
benzyl bromide
[H-].[Na+]
sodium hydride

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

3-(2-dimethylaminoethoxy)-10-benzyl-9(10H)-acridinone [IV; R' is C6H5CH2, R" is H, --O--Y--N=Z is 3--O--CH2CH2N(CH3)2 ], m.p. 134°-136° C. (light yellow powder). The intermediate 3-chloro-10-benzyl-9(10H)-acridinone, m.p. 186°-190° C. (yellow crystals) was prepared from 3-chloro-9(10H)-acridinone and benzyl bromide with sodium hydride in dimethylformamide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04150134uspto-grants-1979_04