Sodium Cyanide → HCID 67373333, compound

HRID 515795Notes

Reaction equation

[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([F:16])[CH:6]=1.[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>C(O)(=O)C.O>[C:1]([C:17]1([NH:4][C:5]2[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([F:16])[CH:6]=2)[CH2:20][CH2:19][CH2:18]1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium cyanide (1.3 g, 26.6 mmol) was added to a mixture of ethyl 4-amino-2-fluorobenzoate (3.25 g, 17.8 mmol) and cyclobutanone (2 mL, 26.6 mmol) in acetic acid (99%, 40 mL) hooked up to a NaOH scrubber and the resulting mixture was heated to 80° C. overnight. The mixture was cooled to room temperature and poured in water. The pink precipitate was filtered, washed with water, and redissolved in DCM (100 mL). The organic layer was washed with a saturated solution of sodium bicarbonate (4×), dried over sodium sulfate, and evaporated to dryness to afford 3.9 g of ethyl 4-((1-cyanocyclobutyl)amino)-2-fluorobenzoate as an orange solid. 1H NMR (300 MHz, CDCl3) δ 7.87 (t, 1H), 6.43 (dd, 1H), 6.34 (dd, 1H), 4.55 (s, 1H), 4.36 (q, 2H), 2.91-2.82 (m, 2H), 2.46-2.30 (m, 2H), 2.28-2.13 (m, 2H), 1.39 (t, 3H).

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe pink precipitate was filtered
washwashed with water
dissolutionredissolved in DCM (100 mL)
washThe organic layer was washed with a saturated solution of sodium bicarbonate (4×)
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-a93d9ef9fb2b448986e5abecdcb608ab
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108944B2

Reaction notes

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