Reaktion #63669

Reaktionsgleichung

1,3-dihydroxy-2-chloro-4,6-dinitrobenzene

NaOAc

HCl

SnC12.2H2O

hydrogen

→

diamino resorcinol dihydrochloride

Lösungsmittel

H2O

H2O

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA one-liter Hastalloy C autoclave equipped with a gas dispersion stirrer
2. 2
   Temperaturcooling coil
3. 3
   workup.ADDITIONThe sealed reactor is charged with 400 psi of H2
4. 4
   Sonstigeis brought to 40° C.
5. 5
   Temperaturmaintained between 40°C.-50° C. during the course of the reaction
6. 6
   TemperaturH2 pressure is maintained between 100-400 psi during the reaction
7. 7
   SonstigeThe crude product with the catalyst is isolated by filtration
8. 8
   Sonstigethe catalyst is removed by filtration
9. 9
   workup.ADDITIONH2O (100-300 ml) is added to the filtrate along with 500 ml of HCl
10. 10
    Sonstigethe catalyst-free material is precipitated from the brown solution
11. 11
    SonstigeRecrystallization
12. 12
    Sonstigethe semi-pure material can be isolated
13. 13
    Sonstigeair dried

Vorschrift

A one-liter Hastalloy C autoclave equipped with a gas dispersion stirrer and cooling coil is charged with 117.3 g (0.5 mole) of 1,3-dihydroxy-2-chloro-4,6-dinitrobenzene, 400 ml of glacial acetic acid, 41 g (~0.5 mole) of NaOAc, ~7.0 g of 10 percent Pd/C and 100 ml of H2O. The sealed reactor is charged with 400 psi of H2 and the temperature is brought to 40° C. and maintained between 40°C.-50° C. during the course of the reaction. After a brief induction period, the uptake of hydrogen becomes extremely rapid and H2 pressure is maintained between 100-400 psi during the reaction. Upon completion, no further uptake of H2 is observed. The reactor is cooled to room temperature, opened and 400 ml of concentrated HCl containing ~10 g of SnC12.2H2O is added to the reaction mixture. The crude product with the catalyst is isolated by filtration. This material is dissolved in 200 g of H2O at 85° C. and the catalyst is removed by filtration. H2O (100-300 ml) is added to the filtrate along with 500 ml of HCl and the catalyst-free material is precipitated from the brown solution. Recrystallization may be carried out in the existing solvent or the semi-pure material can be isolated and air dried to afford 100 g of crude diamino resorcinol dihydrochloride, 4,6-diamino-1,3-benzenediol dihydrochloride (96.8 mole percent yield based on the 1,3-dihydroxy-2-chloro-4,6-dinitrobenzene).

Quelle