Ammonium Chloride → Ethyl 1-(4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662025

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11](=[C:17]([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:4][CH:3]=1.[CH3:20]OC(OC)N(C)C.[NH4+].[Cl-]>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:20]=[CH:19][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 2-(4-fluorophenylcarbamoyl)-3-methylbut-2-enoate (1.85 g, 6.97 mmol) and N,N-dimethylformamide dimethyl acetal (5 mL, 37.45 mmol) is stirred at 90° C. for 90 min. After the reaction is cooled, EtOAc (30 mL) and saturated NH4Cl solution (20 mL) are added. The organic phase is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (10:1). The fractions containing product are concentrated, and the residue is mixed with ether to give 1.2 g of yellow solid which is filtered and discarded. The filtrate is concentrated and purified again by silica gel column chromatography eluting with DCM:MeOH (20:1) to give the product (500 mg, 26% yield). MS (m/z): 276.1 (M+H).

Workup

temperatureAfter the reaction is cooled
customThe organic phase is separated
customdried
concentrationconcentrated
customThe residue is purified by silica gel column chromatography
washeluting with DCM:MeOH (10:1)
additionThe fractions containing product
concentrationare concentrated
additionthe residue is mixed with ether

Sources & evidence

ORD record: ord-b4bec93afae042889ba97f088d11eea0
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030302B2

Linked notes

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