(3-Bromo-7-fluoro-quinolin-6-yl)-acetic acid methyl ester → (3-Bromo-7-fluoro-quinolin-6-yl)-acetic acid

HRID 655253Notes

Reaction equation

HRID 655253 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[F:15])[N:11]=[CH:10][C:9]([Br:16])=[CH:8]2>[OH-].[Na+]>[Br:16][C:9]1[CH:10]=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][C:5]([CH2:4][C:3]([OH:17])=[O:2])=[C:14]([F:15])[CH:13]=2

Participants

3

Reactant 1

HCID 68706227(3-Bromo-7-fluoro-quinolin-6-yl)-acetic acid methyl ester

Product 1

HCID 59320411(3-Bromo-7-fluoro-quinolin-6-yl)-acetic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of (3-bromo-7-fluoro-quinolin-6-yl)-acetic acid methyl ester (13.9 g, 46.6 mmol) in 72 mL of aqueous NaOH (2N) was heated to reflux for 2 hrs then cooled to r.t. The mixture was washed with dichloromethane (50 mL×2) and the aqueous phase acidified with 5N hydrochloric acid to pH 4. The white precipitate was collected via filtration, washed with water and dried. 11.0 g of the title compound was obtained as white powder in 83.3% yield. 1H NMR (DMSO-d6): δ 12.64 (s, 1H), 8.94˜8.95 (d, 1H), 8.72˜8.72 (m, 1H), 7.94˜7.97 (d, 1H), 7.77˜7.81 (d, 1H), 3.85 (s, 2H). LC-MS: 283.9 (M++1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hrs
  3. washThe mixture was washed with dichloromethane (50 mL×2)
  4. filtrationThe white precipitate was collected via filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8b8314d25b7541bab536f75ca7f41c95
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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