3-Methylquinoline-8-sulfonic acid → HCID 19426733, compound

HRID 2400134Notes

Reaction equation

HRID 2400134 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[S:12]([OH:15])(=[O:14])=[O:13]>O.Cl.C(O)C.[Rh]>[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[C:6]([S:12]([OH:15])(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

6

Reactant 1

HCID 193824103-Methylquinoline-8-sulfonic acid

Product 1

HCID 19426733HCID 19426733, compoundYield 68.4%

Reagents, catalysts & solvents 4

HCID 23948RhodiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

20 g (90 mmoles) of 3-methylquinoline-8-sulphonic acid is placed in a mixture of 200 ml of water and 25 ml of 12N hydrochloric acid. 6 g of 5% rhodium on charcoal catalyst is added and the reaction mixture is heated at 70° C. for 16 hours. The catalyst is filtered and washed with hot water and the filtrate is evaporated to provide a residue which is dissolved in 50 ml of ethanol. After evaporation of ethanol the residue is dried over phosphorus pentoxide at 50° C. 14 g of product is obtained.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with hot water
  3. customthe filtrate is evaporated
  4. customto provide a residue which
  5. customAfter evaporation of ethanol the residue
  6. dry with materialis dried over phosphorus pentoxide at 50° C

Sources & evidence

ORD record
ord-745e0aeb36104b278a49f869ae85e7be
Source dataset
uspto-grants-1995_09
Patent number
US05453430

Reaction notes

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