KlementineJBS
commented
1 year ago 19.01.23
- Suspended 1-naphthylamine (409.5 mg, 2.86 mmol) in HCl (17%, 18 mL)
- Cooled to 0 C
- Added NaNO2 (286.1 mg)
reaction went a dark orange-brown colour upon addition of nitrite
- Stirred on ice from 11 am til 1.45 pm and then TLC'd - needed to use diethyl ether to dissolve
Diazo intermediate and azide both present. TLC'd against azide SM recovered from #53 and determined that azide is top spot and diazo compound is middle spot.
- Removed ice water and allowed to stir at rt from 2.15 pm
- TLC'd again at 3.30 pm
- Extracted with diethyl ether (4 x 20 mL)
- Washed with NaHCO3 (2 x 50 mL) and brine (2 x 50 mL)
- Dried over mag sulphate
Obtained a transparent red solution.
- Rotovapped
Empty vial: 15.7172 Full vial: 15.8825 Mass: 165.3 mg (0.978 mmol, 34%)
Link to HIRAC, and master page. Here following a procedure from Pagoti et al. which varies slightly from HIRAC.
for 400 mg (2.79 mmol) of SM:
KBS22 Azidation of 1-naphthylamine.docx
Next attempt is #56
Reaction scheme
Notes
Outcome
Unpurified: 165.3 mg (0.978 mmol, 34%)
Purified: 108.5 mg, 22%