2,3,4-Trichloro-1,5-dinitrobenzene → 4,6-Diaminoresorcinol

HRID 1460863Notes

Reaction equation

HRID 1460863 reaction equation
ClC1C=CC=C(Cl)C=1Cl.[N+]([O-])(O)=O.S(=O)(=O)(O)O.[N+]([O-])(O)=O.ClC1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(Cl)C=1Cl.[OH:38][C:39]1[C:44]([N+:45]([O-])=O)=[CH:43][C:42]([N+:48]([O-])=O)=[C:41]([OH:51])[C:40]=1Cl>CO.O.[Pd]>[NH2:45][C:44]1[C:39]([OH:38])=[CH:40][C:41]([OH:51])=[C:42]([NH2:48])[CH:43]=1

Participants

7

Reactant 4

HCID 228752,3,4-Trichloro-1,5-dinitrobenzeneHCID 111072901,3-Benzenediol, 2-chloro-4,6-dinitro-HCID 67931851HCID 67931851, compoundHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 4588214,6-Diaminoresorcinol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Because of the difficulties mentioned it has been tried to obtain diaminoresorcinol from another starting material. Thus, in EP 266,222 it is proposed to nitrate 1,2,3-trichlorobenzene in a sulphuric acid/nitric acid mixture to 1,2,3-trichloro-4,6-dinitro-benzene and to convert this compound, using an alkali metal hydroxide in methanol/water, into 1,3-dihydroxy-2-chloro-4,6-dinitrobenzene. The reduction of the latter compound on a Pd/activated charcoal catalyst gives diaminoresorcinol. However this process has the disadvantage that the dihydroxy compound of the second process step must be extracted with ethyl acetate, as a consequence of which the space yield drops to about 75 g/l (0.32 mole/l); after the said extraction the dihydroxy compound is isolated by evaporation of the ethyl acetate phase.

Sources & evidence

ORD record
ord-0f8c8fb349ec484f8780350682af36e3
Source dataset
uspto-grants-1991_12
Patent number
US05072053

Reaction notes

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