Lithium Hydroxide → 3-(1-(4-Methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acid

HRID 1023171Notes

Reaction equation

HRID 1023171 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:25])=[CH:5][CH:4]=1.C1COCC1.CO.[Li+].[OH-]>O>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 86680414Ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)propanoate

Product 1

HCID 866804133-(1-(4-Methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)propanoate (0.76 g, 2.07 mmol) in 1:1 THF/methanol (20 mL) was added a solution of LiOH (0.26 g, 6.21 mmol) in water (5 mL). The reaction mixture was stirred at room temperature for 3 h. Solvents were concentrated and the reaction mixture was acidified with citric acid solution to pH 6. Solid was filtered and dried to afford 3-(1-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)propanoic acid as a pale brown solid (0.6 g, 86%). 1HNMR 400 MHz, DMSO-d6: δ 2.46-2.51 (m, 2H), 2.65-2.87 (m, 4H), 2.89 (t, J=16.00 Hz, 2H), 3.71 (s, 3H), 5.05 (s, 2H), 6.85-6.87 (m, 3H), 6.96-6.99 (m, 1H), 7.08 (s, 1H), 7.14-7.16 (m, 2H), 12.08 (s, 1H). LCMS: RT 2.023 min; LCMS (ES-API), RT; 0.81 min; m/z 340.0 [M−H]−.

Workup

  1. concentrationSolvents were concentrated
  2. filtrationSolid was filtered
  3. customdried

Sources & evidence

ORD record
ord-54a929a32d904c938170bf65bc1a45eb
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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