Sodium hydride → (E)-3-(8-Methoxyquinolin-2-yl)acrylic acid

HRID 868973Notes

Reaction equation

[H-].[Na+].COP([CH2:9][C:10]([O:12]C)=[O:11])(OC)=O.[CH3:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH:26]=O)[CH:22]=[CH:21]2.O.[OH-].[Li+]>O1CCCC1.O>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23](/[CH:26]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:22]=[CH:21]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of sodium hydride (60%) (0.8 mg, 20.0 mmol) in tetrahydrofuran (80 mL) was added methyl 2-(dimethoxyphosphoryl)acetate (2.65 mg, 12 mmol) dropwise at 0° C. After the addition was completed, the mixture was stirred for 30 min at 0° C. A solution of 8-methoxyquinoline-2-carbaldehyde (1.87 g, 10.0 mmol) in tetrahydrofuran (20 mL) was then added dropwise over a period of 50 min. The mixture was stirred at 0° C. for 1 h. A solution of lithium hydroxide hydrate (1.26 g, 30.0 mmol) in water (20 mL) was added cautiously to the solution. The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. To the residue was added water (20 mL), and the pH of the aqueous layer was then adjust to 4 with 1 N hydrogen chloride solution. The precipitate was collected by filtration and then dried in vacuum to give 1.9 g of the product as a white solid. MS (ESI): m/z 230.1 [M+H]+.

Workup

additionAfter the addition
stirringThe mixture was stirred at 0° C. for 1 h
stirringThe resulting mixture was stirred at room temperature overnight
concentrationThe reaction mixture was concentrated under reduced pressure
additionTo the residue was added water (20 mL)
filtrationThe precipitate was collected by filtration
customdried in vacuum

Sources & evidence

ORD record: ord-b4c6c8424e4f43ccb7cde0aa72bb29e7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969349B2

Reaction notes

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