Acridine, 9-chloro-1-nitro- → HCID 178486225, compound

HRID 463687Notes

Reaction equation

HRID 463687 reaction equation
[Cl:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]([N+:16]([O-:18])=[O:17])=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.Cl.[CH3:20][N:21]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[NH2:22]>CN(C)C=O>[ClH:1].[CH3:20][N:21]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[N:22]=[C:2]1[C:15]2[C:14]([N+:16]([O-:18])=[O:17])=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 2

HCID 146341Acridine, 9-chloro-1-nitro-HCID 20158328HCID 20158328, compound

Product 1

HCID 178486225HCID 178486225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.3 g of 9-chloro-1-nitroacridine, 1.65 g of N-methyl-N-(2-thiazolyl)hydrazine hydrochloride and 100 ml of dimethylformamide is stirred at room temperature for about 18 hours. The dark red solution is evaporated, whereupon the residue is made alkaline with sodium carbonate solution and extracted with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated. The residue is taken up in ethanol, acidified with ethanolic hydrochloric acid and the product is precipitated by the addition of ether. After filtration and washing with ether and petroleum ether, the hygroscopic salt is dried over phosphorus pentoxide. There is obtained 1-nitro-9-acridanone methyl (2-thiazolyl)hydrazone hydrochloride of melting point 185° (decomposition).

Workup

  1. customThe dark red solution is evaporated, whereupon the residue
  2. extractionextracted with methylene chloride
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customthe product is precipitated by the addition of ether
  7. filtrationAfter filtration
  8. washwashing with ether and petroleum ether
  9. dry with materialthe hygroscopic salt is dried over phosphorus pentoxide

Sources & evidence

ORD record
ord-0e64e744c1024c63a60d7e7ad029bd55
Source dataset
uspto-grants-1985_10
Patent number
US04544659

Reaction notes

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