Sodium Azide → Methyl 4-azido-2-(trifluoromethyl)nicotinate

HRID 1170895Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[N:5]=[CH:4][CH:3]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.O>[N:16]([C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[N:5]=[CH:4][CH:3]=1)=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of methyl 4-chloro-2-(trifluoromethyl)nicotinate (9.75 g, 40.7 mmol) in DMF (300 mL) is added sodium azide (21.2 g, 326 mmol). The solution is warmed to 45° C. for 3 hours and then to 50° C. for 1 hour. The reaction is diluted with water (300 mL) and extracted with ether-pentane (1:1, ca. 1 L). The organic layer is back extracted with water (3×). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 9.50 g (95%) of the title compound as a brown oil: 1H NMR (400 MHz, CD3OD), 8.651 (d, 1H), 7.603 (d, 1H), 3.878 (s, 3H).

Workup

extractionextracted with ether-pentane (1:1, ca. 1 L)
extractionThe organic layer is back extracted with water (3×)
dry with materialThe organic layer is dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2d818e6ad4c64f549566701e43cf6afb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829572B2

Reaction notes

Loading…