N,N-Dimethyl-1,3-propanediamine → 7-chloro-3-(3,4-dichlorophenyl)1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone

HRID 1578078Notes

Reaction equation

HRID 1578078 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[Cl:8][C:9]1[CH:22]=[C:21]2[C:12]([N:13]([OH:33])[C:14]3[CH2:15][CH:16]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[CH2:17][C:18](=O)[C:19]=3[C:20]2=[O:23])=[CH:11][CH:10]=1>C(O)C>[Cl:8][C:9]1[CH:22]=[C:21]2[C:12]([N:13]([OH:33])[C:14]3[CH2:15][CH:16]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[CH2:17][C:18](=[N:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[C:19]=3[C:20]2=[O:23])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 10250916HCID 10250916, compound

Product 1

HCID 103909737-chloro-3-(3,4-dichlorophenyl)1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1.4 g of N,N-dimethyl-1,3-propanediamine in 10 ml of ethanol is added dropwise to a stirred, cooled mixture of 4.1 g of 7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-10-hydroxy-1,9(2H,10H)acridinedione in 100 ml of ethanol. The mixture is stirred at room temperature overnight and evaporated to dryness in vacuo. The residue is recrystallized from ethanol to give 7-chloro-3-(3,4-dichlorophenyl)1-[[3-(dimethylamino)propyl]imino]-1,3,4,10-tetrahydro-10-hydroxy-9(2H)acridinone; mp 208°-210° C.

Workup

  1. temperaturecooled
  2. customevaporated to dryness in vacuo
  3. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-783ab628ff5a41559578b397c4f22bfe
Source dataset
uspto-grants-1981_09
Patent number
US04291034

Reaction notes

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