Sodium Hydroxide → 2-(Quinolin-6-yl)propanoic acid

HRID 655217Notes

Reaction equation

HRID 655217 reaction equation
C[O:2][C:3](=[O:16])[CH:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)[CH3:5].[OH-].[Na+]>>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:16])=[O:2])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 57691200Methyl 2-(quinolin-6-YL)propanoate

Product 1

HCID 190360062-(Quinolin-6-yl)propanoic acid

Procedure

2-Quinolin-6-yl-propionic acid methyl ester containing 10% 2-methyl-2-quinolin-6-yl-propionic acid methyl ester (7.7 g, 35.8 mmol) and 2 N aq. NaOH (27 ml) was heated to reflux for 4 hours until the reaction mixture became clear. After cooling to room temperature the mixture was extracted with dichloromethane and the aqueous layer was acidified with concentrated hydrochloric acid to pH 4-5. Ethyl acetate (30 ml) was added and stirred for 10 min, the resulting solid was filtered off to obtain product, which was re-crystallized twice from methanol to return the title compound (5.3 g, 73.7%): 1H NMR 300 MHz (DMSO-d6) δ12.43 (s, 1H), 8.86 (d, 1H), 8.33 (d, 1H), 7.99-7.86 (m, 2H), 7.72-7.49 (m, 2H), 3.92 (q, 1H), 1.48 (d, 3H). ES− MS m/z: 200 [M−H+]−, 400 (dimer).

Workup

  1. temperatureto reflux for 4 hours until the reaction mixture
  2. extractionwas extracted with dichloromethane
  3. additionEthyl acetate (30 ml) was added
  4. filtrationthe resulting solid was filtered off
  5. customto obtain product, which
  6. customwas re-crystallized twice from methanol

Sources & evidence

ORD record
ord-7f8c1e38f86d4e57b8a3108735fb175b
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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