1-Chloro-2-nitrobenzene → Hydrazine,1,2-bis(2-chlorophenyl)-

Temperatur

60 °C

To a stirred solution of 50% NaOH (1 mL, 12.5 mM) was added 2-chloronitrobenzene (3.14 g, 20 mM) and the resulting solution was heated to 60° C. Zinc dust (3 g, 46 mM) was added at such a rate as to keep the temperature of the reaction below 80° C. After the addition was complete, 20% NaOH (6 mL, 30 mM) was added followed by water (10 mL). An additional quantity of zinc dust (4 g, 71 mM) was then added in one portion. The resulting mixture was stirred between 75°-80° C. for 30 minutes. The mixture was cooled to room temperature and the solids were filtered and extracted with ether. The combined filtrates were dried over Na2SO4 and concentrated. Purification via flash column chromatography gave a solid which was then triturated with ether. This afforded the titled product as a yellow solid (1.2 g, 60%). NMR (CDCl3): 7.31 (m, 2H), 7.11 (m, 2H), 6.94 (m, 2H), 6.76 (m, 2H), 6.21 (br s, 2H). MS(CI): 253(M+1).

1. customthe temperature of the reaction below 80° C
2. additionAfter the addition
3. temperatureThe mixture was cooled to room temperature
4. filtrationthe solids were filtered
5. extractionextracted with ether
6. dry with materialThe combined filtrates were dried over Na2SO4
7. concentrationconcentrated
8. customPurification via flash column chromatography
9. customgave a solid which
10. customwas then triturated with ether

ORD-Eintrag

ord-cb47eb815b534ed1bd2682f237f75b73

Quelldatensatz

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05652239