Bromoform → 2-Methoxy-2-(quinolin-5-yl)acetic acid
Reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:11]=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+].[CH:15](Br)(Br)Br.[OH-:19].[K+].[CH3:21][OH:22]>CO.O1CCOCC1>[CH3:15][O:13][CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)[C:21]([OH:22])=[O:19]Participants
Procedure
To an ice-cold solution of quinoline-5-carbaldehyde (3.5 g, 22.3 mmol) in anhydr MeOH (30 mL) and anhydr dioxane (30 mL) was added several drops of a solution of KOH (6.2 g, 113.4 mmol) in MeOH (30 mL). Bromoform (2.5 mL, 30 mmol) was added, then the remaining KOH/MeOH solution was added over a period of 10 min. After stirring for 30 min the reaction mixture was allowed to warm slowly to room temperature overnight then concentrated to dryness. After dissolving in a minimum amount of H2O, the residue was acidified to pH 1 with concentrated HCl. The aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 2-methoxy-2-(quinolin-5-yl)acetic acid as a semisolid (2.8 g, 58% yield). The product was used without further purification.
Workup
- concentrationthen concentrated to dryness
- dissolutionAfter dissolving in a minimum amount of H2O
- extractionThe aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction
- washThe combined organics were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-52f421a6842e4ca3b2f312e65196e3fb
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343970B2
Reaction notes
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