Sodium Hydroxide → (3-Bromoquinolin-6-yl)acetic acid

HRID 655238Notes

Reaction equation

HRID 655238 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([Br:15])=[CH:8]2.[OH-].[Na+]>>[Br:15][C:9]1[CH:10]=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][C:5]([CH2:4][C:3]([OH:16])=[O:2])=[CH:14][CH:13]=2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 58190594HCID 58190594, compound

Product 1

HCID 59320341(3-Bromoquinolin-6-yl)acetic acidYield 73.5%

Procedure

A mixture of (3-bromo-quinolin-6-yl)-acetic acid methyl ester (14.8 g, 52.8 mmol) and aqueous 2 N NaOH (80 ml, 160 mmol) was heated under reflux for 1.5 hours until reaction mixture became clear. After cooling down to room temperature the reaction mixture was washed with dichloromethane then the water layer was acidified with concentrated hydrochloric acid to pH 4. A white precipitate was filtered off the stirred in refluxing methanol, filtered and dried in vacuo to give the product title compound as a white solid (10.3 g, 73.5%). (300 MHz, DMSO-d6): 12.52 (b, 1H), 8.91 (d, 1H), 8.69 (d, 1H), 7.99 (d, 1H)), 7.82˜7.70 (m, 2H), 3.80 (s, 2H). ES-MS m/z: 266 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours until reaction mixture
  3. washwas washed with dichloromethane
  4. filtrationA white precipitate was filtered off the
  5. temperaturein refluxing methanol
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4915d6107b9949918f63514d289d1e28
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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