Hydrochloric Acid → 1-[6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH2:16][C:17]1[CH:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=1)=[O:4].O.C[O-].[Na+].Cl.[F:29][C:30]([F:34])([F:33])[CH2:31][OH:32]>>[F:29][C:30]([F:34])([F:33])[CH2:31][O:32][C:20]1[N:19]=[CH:18][C:17]([CH2:16][O:15][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:5]=2[C:3]([OH:2])=[O:4])=[CH:22][CH:21]=1Participants
6
Conditions
- Temperature
- 165 °C
Procedure
To a solution of 0.30 g of 1-(6-chloro-pyridin-3-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester in 4 ml 2,2,2-trifluoroethanol containing 5% of water was added 0.55 g sodium methoxide. The reaction was heated to 165° C. for 1 h using a microwave reactor. The reaction was then poured into ice-water, the pH was adjusted to 4 using 2 M hydrochloric acid and the precipitated product was collected by filtration and dried in vacuo yielding 0.22 g of 1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid.
Workup
- filtrationthe precipitated product was collected by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-8a100012c0b14985b7fd85fdbaa9cd83
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919628B2
Reaction notes
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