HCID 59204906, compound → HCID 68548000, compound

HRID 2241923Notes

Reaction equation

HRID 2241923 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:12]([F:22])[CH:11]=1)=[O:8]>[Pt](=O)=O.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)=[C:12]([F:22])[CH:11]=1)=[O:8]

Participants

4

Reactant 1

HCID 59204906HCID 59204906, compound

Product 1

HCID 68548000HCID 68548000, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-chloro-N-[3-fluoro-4-(pyridin-4-yl)phenyl]-2-hydroxybenzamide (compound of Reference Example 186; 0.104 g, 0.303 mmol), platinum(IV) oxide (0.100 g, 0.440 mmol) and methanol (10 ml) was stirred under ice cooling for 5 hours under hydrogen atmosphere. The reaction mixture was filtered, and the residue obtained by evaporation of the solvent of the filtrate under reduced pressure was purified by column chromatography on silica gel. 2N Hydrochloric acid was added to the obtained purified substance, and the mixture was refluxed for 1 hour. The solvent was evaporated under reduced pressure to give the title compound (0.021 g, 18%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe residue obtained by evaporation of the solvent of the filtrate under reduced pressure
  3. customwas purified by column chromatography on silica gel
  4. addition2N Hydrochloric acid was added to the obtained
  5. custompurified substance
  6. temperaturethe mixture was refluxed for 1 hour
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-373f4803b0ba4649b5ddcaa120423416
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

Loading…