Methyl 2-(3-bromo-5,7-difluoroquinolin-6-yl)acetate → 2-(3-Bromo-5,7-difluoroquinolin-6-yl)acetic acid

HRID 655249Notes

Reaction equation

HRID 655249 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6]([F:17])=[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)=[C:6]([F:17])[C:5]([CH2:4][C:3]([OH:18])=[O:2])=[C:14]([F:15])[CH:13]=2

Participants

3

Reactant 1

HCID 59320329Methyl 2-(3-bromo-5,7-difluoroquinolin-6-yl)acetate

Product 1

HCID 593204392-(3-Bromo-5,7-difluoroquinolin-6-yl)acetic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of (3-bromo-5,7-difluoro-quinolin-6-yl)-acetic acid methyl ester (10.0 g, 31.6 mmol) in 48 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. 9.6 g of the title compound was obtained as white powder in 100% yield. 1H NMR (DMSO-d6): δ 12.87 (s, 1H), 9.05 (s, 1H), 8.76 (s, 1H), 7.75˜7.79 (d, 1H), 3.87 (s, 2H).

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-a0fc3d74fa4241688009696aaef8102e
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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