Hydrochloric Acid → (E)-3-[2-fluoro-4-(2-pyridylmethoxy)phenyl]-2-propenoic acid

HRID 632513Notes

Reaction equation

[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[F:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:14]=[CH:13][C:10]=1C=O.N1CCCCC1.Cl>O.N1C=CC=CC=1>[F:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:14]=[CH:13][C:10]=1/[CH:3]=[CH:2]/[C:1]([OH:7])=[O:6]

Participants

Conditions

Temperature: 75 °C

Procedure

To 1.8 g of malonic acid were added 18 mL of pyridine, 2.0 g of 2-fluoro-4-(2-pyridylmethoxy)benzaldehyde and 0.21 mL of piperidine. The mixture was stirred at 75° C. for 1.5 hours and further stirred at 95° C. for 1 hour. The reaction mixture was cooled with ice, water was added thereto, and 10% hydrochloric acid was added to adjust the pH to 4. The resulting precipitate was separated by filtration to give 2.0 g of the title compound (85% yield).

Workup

stirringfurther stirred at 95° C. for 1 hour
additionwas added
customThe resulting precipitate was separated by filtration

Sources & evidence

ORD record: ord-a2cf7d6573db4c79abb7c2b76983edcb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321752B2

Reaction notes

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