Sodium Hydroxide → 2-(7-Fluoroquinolin-6-yl)acetic acid

HRID 655223Notes

Reaction equation

HRID 655223 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[F:18])[N:14]=[CH:13][CH:12]=[CH:11]2)(C)(C)C.[OH-].[Na+]>>[F:18][C:17]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[CH2:7][C:6]([OH:19])=[O:5]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 68534606(7-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester

Product 1

HCID 468356122-(7-Fluoroquinolin-6-yl)acetic acidYield 79.8%

Conditions

Temperature
90 °C

Procedure

A mixture of (7-fluoro-quinolin-6-yl)-acetic acid tert-butyl ester (3.67 g) and 4N aquous sodium hydroxide (14.8 mL) were heated at 90° C. for 3 h. The solution was extracted with ethyl acetate. The aqueous layer was adjusted to acidic pH with acetic acid and filtered and dried to afford the title compound (2.3 g, 79.8%). 1H NMR (300 MHz, DMSO-d6) δ 12.52 (1H, s), 8.88˜8.90 (d, 1H), 8.34˜8.38 (d, 1H), 7.97˜7.99 (d, 1H), 7.73˜7.76 (d, 1H), 7.50˜7.54 (m, 1H), 3.85 (s, 2H). ES-MS m/z: 206.2 (M+1).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-ad3d82b548b648d4b050f58b130be31e
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

Loading…