Ammonia → N-(2-dimethylaminoethyl)-9-amino-7-nitroacridine-4-carboxamide dihydrochloride

HRID 280720Notes

Reaction equation

HRID 280720 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]2[C:7]([NH:8][C:9]3[C:10]([C:19](O)=[O:20])=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:22](C1C=C2C(N=C3C(=C2[Cl:39])C=CC=C3C(Cl)=O)=CC=1)([O-])=O.[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46][NH2:47].N>C1(O)C=CC=CC=1>[ClH:39].[ClH:39].[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46][NH:47][C:19]([C:10]1[C:9]2[C:14](=[C:15]([NH2:22])[C:16]3[C:7]([N:8]=2)=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:17]=3)[CH:13]=[CH:12][CH:11]=1)=[O:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 66053N,N-DimethylethylenediamineHCID 5420897-Nitro-9-oxo-9,10-dihydroacridine-4-carboxylic acidHCID 233211989-Chloro-7-nitroacridine-4-carbonyl chloride

Product 1

HCID 23321196N-(2-dimethylaminoethyl)-9-amino-7-nitroacridine-4-carboxamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

The above 7-nitro-4-carboxyacridanone was converted to 7-nitro-9-chloroacridine-4-carbonyl chloride (II, Z=Cl, R2 =7-NO2, R3 =Cl), and treated with N,N-dimethylethylenediamine followed by dry ammonia in phenol by the methods outlined in Example A above to give N-(2-dimethylaminoethyl)-9-amino-7-nitroacridine-4-carboxamide dihydrochloride (compound 20 of Table I), m.p. 316°-318° C.

Sources & evidence

ORD record
ord-d51b380cd14c48299516efe371fd9726
Source dataset
uspto-grants-1986_05
Patent number
US04590277

Reaction notes

Loading…