Sulfuric Acid → 1-chloro-10-methyl-9(10H)-acridinone

HRID 26466Notes

Reaction equation

HRID 26466 reaction equation
CN(C)CCO[C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl:23]C1C2C(=O)C3C(=CC=CC=3)NC=2C=CC=1.ClC1C=C(NC2C=CC=CC=2C(O)=O)C=CC=1.S(=O)(=O)(O)O>C(O)C>[Cl:23][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 832932-((3-Chlorophenyl)amino)benzoic acidHCID 124915971-Chloroacridin-9(10H)-oneHCID 20296389HCID 20296389, compound

Product 1

HCID 202650031-chloro-10-methyl-9(10H)-acridinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-dimethylaminoethoxy)-10-methyl-9(10H)-acridinone [IV; R' is CH3, R" is H, --O--Y--N=Z is 1--O--CH2CH2N(CH3)2 ], hydrochloride salt, m.p. 237°-241° C. (tan granules from methanol-ether). The intermediate 1-chloro-10-methyl-9(10H)-acridinone, m.p. 183°-186° C. (pale yellow granules from ethanol) was prepared by N-methylation of 1-chloro-9(10H)-acridinone, in turn prepared by cyclization of 2-(m-chlorophenylamino)benzoic acid with sulfuric acid.

Sources & evidence

ORD record
ord-58421d0dfa8145088f38952d4daed6e8
Source dataset
uspto-grants-1979_04
Patent number
US04150134

Reaction notes

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