KBS23-1 - Azidation of 1-naphthylamine about usyd_phd_eln

[KlementineJBS]

29.08.22

1. Dissolved 1-naphthylamine (243.5 mg, 1.70 mmol) in HCl (10.2 M, 2 mL) and water (8 mL)

2. Cooled to 0 C
3. Added sodium nitrite (162 mg) dissolved in water (4 mL)

4. Stirred for 15 minutes
5. Added sodium azide (136.2 mg) and stirred at room temp for 1 hour

TLC indicated completion

[KlementineJBS]

30.08.22

6. Extracted with diethyl ether (4 x 30 mL). Organic layer was a deep crimson colour.

7. Dried over MgSO4 and rotovapped down
8. Left on high vac from 3.20 pm - 5.20 pm

Empty vial: 15.7161
Full vial: 15.9077
Mass: 191.6 mg

[KlementineJBS]

31.08.22

IR

KBS23-1 cr.zip
KBS23-1 cr.pdf

Peaks at 3050 (C-H stretch), 2104 (azide stretch). Double check CH stretch wavenumber

NMR

1H NMR (300 MHz, Chloroform-d) δ 8.17 – 8.05 (m, 1H), 7.85 – 7.78 (m, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.56 – 7.41 (m, 3H), 7.30 – 7.23 (m, 1H). **In agreement with literature, **

KBS23-1 cr_1.zip
KBS23-1 cr processed.pdf