Water → 3,6-Dihydroxy-4,5-dimethylacridine

HRID 2309730

Reaction equation

HRID 2309730 reaction equation
[OH:1]C1C=CC2C(C=1)=NC1C(=CC=C(O)C=1)C=2.NC1C=CC2C(C=1)=NC1C(=CC=C(N)C=1)C=2.N[C:34]1[CH:35]=[CH:36][C:37]2[C:46]([C:47]=1[CH3:48])=[N:45][C:44]1[C:39](=[CH:40][CH:41]=[C:42](N)[C:43]=1[CH3:49])[CH:38]=2.S(=O)(=O)(O)O.[OH2:56]>>[OH:56][C:34]1[CH:35]=[CH:36][C:37]2[C:46]([C:47]=1[CH3:48])=[N:45][C:44]1[C:39](=[CH:40][CH:41]=[C:42]([OH:1])[C:43]=1[CH3:49])[CH:38]=2

Participants

6

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 7099ProflavineHCID 38518Acridine, 3,6-diamino-4,5-dimethyl-HCID 135482596Acridine-3,6-diol

Product 1

HCID 1358383693,6-Dihydroxy-4,5-dimethylacridine

Procedure

3,6-Dihydroxy-4,5-dimethylacridine is prepared by the procedure of Benda, L., Ber., 45, 1787 (1912), for the preparation of 3,6-dihydroxyacridine from 3,6-diaminoacridine. In this reaction 3,6-diamino-4,5-dimethylacridine is heated in a bomb with two parts of water and one part concentrated sulfuric acid at 200° C. for 8 hours. The reaction mixture is diluted with water and the crude solid collected by filtration. This material is purified by dissolution in excess 1N sodium hydroxide, followed by treatment with charcoal and then acidification with acetic acid, giving an orange solid.

Workup

  1. filtrationthe crude solid collected by filtration
  2. customThis material is purified by dissolution in excess 1N sodium hydroxide
  3. customacidification with acetic acid, giving an orange solid

Sources & evidence

ORD record
ord-554ba3a361f4426ca723c67c867b6c1c
Source dataset
uspto-grants-1987_09
Patent number
US04696936

Linked notes

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