KBS23-6 - Azidation of 1-naphthylamine

[KlementineJBS]

Link to HIRAC, and master page. Original method from J. Batten's PhD thesis, but a similar method is used by Babin et al..

KBS22 Azidation of 1-naphthylamine.docx

Previous attempt is #146

Reaction scheme

Outcome

1.3785 g (8.15 mmol, 58%)

[KlementineJBS]

1. Dissolved 2.003 g (14 mmol) of 1-naphthylamine in HCl (3.4 M, 14 mL)
2. Put on ice
3. Added NaNO2 (1.2583, 18.2 mmol, 1.3 equiv.) dissolved in water (5 mL) portionwise
4. Stirred on ice for 20 minutes
5. Added NaN3 (1.3683 g, 21 mmol, 1.5 equiv.) at 10.20 am
6. Left stirring on ice

[KlementineJBS]

Worked up at about 11.20 am. Quenched with 10 mL water then extracted with diethyl ether (3 x 75 mL) - had to add more water to dissolve grainy black solids.

Washed combined extracts with water (2 x 100 mL) and brine (100 mL), dried over mag sulphate and rotovapped down.

Vial: 15.6721 Mass: 1.5732 g (9.3 1 mmol, 67%)

[KlementineJBS]

H NMR

KBS23-6 cr_1.zip KBS23-6 cr.pdf

[KlementineJBS]

Column details

Fractions	Vial weight	Mass	% yield
1-3	15.5194	1.3785 g	8.15 mmol, 58%
11-33	15.9173	439.2 mg	3.07 mmol, 22%
35-45	-	-	-

[KlementineJBS]

H NMR

F1-3 is product, clean. F11-33 appears to be SM, and is also mostly clean. F35-45 is junk.

KBS23-6 column.pdf KBS23-6 F35-45_1.zip KBS23-6 F1-3_1.zip KBS23-6 F11-33_1.zip