Methanesulfonic Acid → 8-chloro-5-hydroxy-4-methyl-3-(4-pyrazol-1-ylbenzyl)-1H-quinolin-2-one

HRID 1944306Notes

Reaction equation

HRID 1944306 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:27])[CH:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)=[CH:18][CH:17]=1)[C:12](=O)[CH3:13].CS(O)(=O)=O.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]2[C:3]=1[NH:9][C:10](=[O:27])[C:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=1)=[C:12]2[CH3:13]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 517045Sodium AcetateHCID 86642371N-(2-chloro-5-hydroxyphenyl)-3-oxo-2-(4-pyrazol-1-ylbenzyl)butyramide

Product 1

HCID 674579118-chloro-5-hydroxy-4-methyl-3-(4-pyrazol-1-ylbenzyl)-1H-quinolin-2-oneYield 65.4%

Conditions

Temperature
100 °C

Procedure

A mixture of N-(2-chloro-5-hydroxyphenyl)-3-oxo-2-(4-pyrazol-1-ylbenzyl)butyramide (1.3 g) and methanesulfonic acid (7.0 mL) was heated at 100° C. for 10 minutes. The mixture was cooled to room temperature and then poured into a saturated aqueous solution of sodium acetate. The resulting precipitate was collected by filtration, washed with water and dried to afford title compound as a beige solid (0.81 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8dfc4af395e14fcdae29f398face83f8
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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