Tin tetrachloride → (2-Benzyloxy-phenyl)-hydrazine

The 2-benzyloxyaniline (4.99 g, 25.0 mmol) partially dissolved in conc hydrochloric acid (15 mL) was cooled to less than 0° C. and a solution of the sodium nitrite (2.07 g, 30.0 mmol) in water (10 mL) was added dropwise. The reaction was stirred at the same temp for 30 min, when tin chloride (16.9 g, 75.0 mmol) in hydrochloric acid (10 mL) was added dropwise again keeping temp ca 0° C. The reaction was stored overnight in the fridge. The aqueous was decanted off the resulting black oily gum and triturated with sat NaCl (cf. 50 mL) and then ether:hexane 1:2 (50 mL) before neutralising with 10M NaOH (aq) with external cooling and extracted into ether (2×100 mL). The combined ether layers were washed with water (100 mL) dried (MgSO4) and evaporated to give a brown oil which crystallised on standing (4.52 g, 84%). Material was used crude without further purification.

1. temperaturewas cooled to less than 0° C.
2. customkeeping temp ca 0° C
3. waitThe reaction was stored overnight in the fridge
4. customThe aqueous was decanted off the resulting black oily gum
5. customtriturated with sat NaCl (cf. 50 mL)
6. temperaturewith external cooling
7. extractionextracted into ether (2×100 mL)
8. washThe combined ether layers were washed with water (100 mL)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customto give a brown oil which
12. customcrystallised
13. customwithout further purification

ORD record

ord-f0355b2568bc403098e5f1fc2e2a8fbf

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008279B2