Sulfuric Acid → HCID 20272673, compound

HRID 371371Notes

Reaction equation

HRID 371371 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:18])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:3]=1.OS(O)(=O)=O.NC1C2C(=O)C3C(=C(N)C=C([Cl:51])C=3O)C(=O)C=2C(O)=C(C2C=CC(OC)=CC=2)C=1>O=[Mn]=O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH2:18])[C:10]([Cl:51])=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 208269,10-Anthracenedione, 4,8-diamino-1,5-dihydroxy-2-(4-methoxyphenyl)-HCID 20272684HCID 20272684, compound

Product 1

HCID 20272673HCID 20272673, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

A mixture of 2.1 g of 4,8-diamino-1,5-dihydroxy-2-p-methoxyphenylanthraquinone (which can be prepared from 1,5-dihydroxy-4,8-dinitroanthraquinone, for method see German Offenlegungsschrift No. 3,007,198), 32 g of 60% H2SO4, and 3 g of active MnO2 is stirred for 1 hour at 20°, the mixture is filtered and 1 g of NaCl is added to the filtrate, which contains the corresponding quinoneimine. After stirring for half an hour, the mixture is poured into ice-water and the product is filtered off. The crude product is chromatographed over silica gel using petroleum ether/ether mixtures. The main product obtained is 4,8-diamino-6-chloro-1,5-dihydroxy-2-p-methoxyphenylanthraquinone, m.p. 310° (decomposition); Rf 0.41 (silica gel; 3:2 ether/petroleum ether). 4,8-diamino-7-chloro-1,5-dihydroxy-2-p-methoxyphenylanthraquinone, Rf 0.45 (silica gel; 3:2 ether/petroleum ether) is also formed.

Workup

  1. filtrationthe mixture is filtered
  2. addition1 g of NaCl is added to the filtrate, which
  3. stirringAfter stirring for half an hour
  4. additionthe mixture is poured into ice-water
  5. filtrationthe product is filtered off
  6. customThe crude product is chromatographed over silica gel
  7. customThe main product obtained

Sources & evidence

ORD record
ord-754af909ef5b49fbbf63bc8c4e3bea5c
Source dataset
uspto-grants-1985_07
Patent number
US04532069

Reaction notes

Loading…