Hydrochloric Acid → 3-{6-[1-Methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoic acid

HRID 861011Notes

Reaction equation

C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[C:12]([C:20]([S:23]([CH3:26])(=[O:25])=[O:24])([CH3:22])[CH3:21])[CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH:5]=1.[Li+].[OH-].Cl>C1COCC1>[CH3:26][S:23]([C:20]([C:12]1[CH:13]=[C:14]2[C:19](=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:27])=[O:2])[CH:11]=1)[N:18]=[CH:17][CH:16]=[CH:15]2)([CH3:22])[CH3:21])(=[O:25])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzoic acid methyl ester from Step 1 (1.0 eq.) in THF (0.2M) was added aqueous LiOH (1.0M; 3.0 eq.). The mixture was stirred for 5 h at 60° C., neutralized to pH=5 using aqueous HCl (1M) and extracted with CH2Cl2 (4×). The combined organic extracts were dried over MgSO4, filtered and concentrated. Stirring in Hex:Et2O (1:1) afforded the title compound after filtration.

Workup

extractionextracted with CH2Cl2 (4×)
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated
stirringStirring in Hex

Sources & evidence

ORD record: ord-5bf5b0d2373e4b8690489512cf904019
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153968B2

Reaction notes

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