4-Fluoroaniline → HCID 90187309, compound

HRID 1755211Notes

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].CC([O-])=O.[Na+].[N+:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[C-:19]>Cl.O.CO>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:19]=[N:18][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Fluoroaniline (2.8 g, 26 mmol) was dissolved in 10% HCl and cooled to 0° C. To this solution was carefully added NaNO2 (1.8 g, 26 mmol) dissolved in 10 mL water. In a separate flask, NaOAc (13 g, 96 mmol), and water (25 mL) were added to a solution of ethyl isocyanoacetate (2.0 g, 18 mmol) in methanol (80 mL). This solution was cooled to 0° C. and the diazonium salt of 4-fluoroaniline was carefully added over the course of 15 minutes. Stirring was continued at 0° C. for an additional 15 minutes, after which the flask was removed from the ice bath and stirring was continued for an additional 2 hours. The reaction mixture was then added to 500 mL water and the resulting brown precipitate was collected by filtration and dried in vacuo to obtain 3.8 g of the desired ester (90% yield).

Workup

temperatureThis solution was cooled to 0° C.
customafter which the flask was removed from the ice bath
stirringstirring
waitwas continued for an additional 2 hours
additionThe reaction mixture was then added to 500 mL water
filtrationthe resulting brown precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-71fbb7a070cb4c899455f4ca42356e66
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169261B2

Reaction notes

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