Hydrazine hydrate (1:1) → 5-Bromo-o-toluidine

To a stirred solution of 4-bromo-2-nitrotoluene (2.04 g, 9.44 mmol) (Aldrich Chemical Company) in ethanol (25 mL) was added hydrazine hydrate (1.14 mL, 23.60 mmol) drop-wise. After being stirred for 5 min, a suspension of Raney nickel (˜100 mg) in ethanol (5 mL) was added slowly and carefully. Gas evolution was observed. After gas evolution subsided, the reaction mixture was heated to reflux for 1 h. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated on a rotary evaporator, diluted with water (25 mL) and extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered and concentrated to produce 1.57 g (89.4%) of a colorless oil.

1. additionwas added slowly
2. temperaturethe reaction mixture was heated
3. temperatureto reflux for 1 h
4. filtrationfiltered
5. concentrationThe filtrate was concentrated on a rotary evaporator
6. additiondiluted with water (25 mL)
7. extractionextracted with chloroform (3×100 mL)
8. dry with materialThe combined chloroform extracts were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-de2633dcfed24888bcd15afd8e4b2e25

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06337351B1