Reaktion #1771285

Reaktionsgleichung

7

3,6-Bis(methylcarbamyl)-1,4-dimethoxy-2,5-dinitrobenzene

methanol

hydrochloric acid

→

3,6-Bis(methylcarbamyl)-1,4-dimethoxy-2,5-diaminobenzene

Lösungsmittel

n-butanol acetic acid water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   workup.STIRRINGwith stirring
3. 3
   FiltrationAfter filtering the solution through CELITE
4. 4
   Waschenwashing the filtrate with methanol
5. 5
   Sonstigethe solvent was removed in vacuo
6. 6
   Sonstigethe residue dried for several hours
7. 7
   SonstigeThe dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol
8. 8
   Temperaturby cooling
9. 9
   workup.ADDITIONaddition of ethyl acetate
10. 10
    Sonstige893 mg (88%) yield

Vorschrift

A mixture consisting of 978 mg (2.84 mmol) of 7, 100 mg 5% Pd/C, and 100 mL of methanol was shaken under 50 psi of H2 for 4 hours. Upon completing the reduction, 10 mL of concentrated hydrochloric acid was added to the reaction mixture with stirring. After filtering the solution through CELITE and washing the filtrate with methanol, the solvent was removed in vacuo and the residue dried for several hours. The dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol followed by cooling and then addition of ethyl acetate: 893 mg (88%) yield; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.44; 1H NMR (dimethyl-d6 sulfoxide) δ8.40 (2H, brs, 3- and 6-carbamyl proton), 3.64 (6H, s, methoxys), 2.81 (6H, d, J=4.0 Hz, 3- and 6-carbamyl methyls); mass spectrum (EI mode), m/z 282 (P+).

Quelle