HCID 68825474, compound → HCID 178468675, compound

HRID 1297697Notes

Reaction equation

HRID 1297697 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=[C:13]([C:18]([O:20]CC)=O)[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:7][CH:6]=1)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[N:11]=[CH:12][C:13]([S:14]([CH3:17])(=[O:15])=[O:16])=[C:18]2[OH:20])=[O:23])[CH3:2]

Participants

3

Reactant 1

HCID 68825474HCID 68825474, compound

Product 1

HCID 178468675HCID 178468675, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

To the solution of 4-(2-ethoxycarbonyl-2-methanesulfonyl-vinylamino)-benzoic acid ethyl ester (example 61d) in phosphorous oxychloride (700 mL), Polyphosphoric acid (PPA, 445 g) was added. The resulted mixture was heated at 70 degrees for 8 hours under mechanical stirring. After the reaction, the reaction mixture was cooled to room temperature, and then phosphorous oxychloride was evaporated under reduced pressure. To the residue, water was added. The solid was filtered, collected, washed with water thoroughly, and then dried. Column chromatography gave 4-hydroxy-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (25 g, purity 70%). LC-MS m/e 232 (MH+)

Workup

  1. temperatureThe resulted mixture was heated at 70 degrees for 8 hours under mechanical stirring
  2. customAfter the reaction
  3. customphosphorous oxychloride was evaporated under reduced pressure
  4. additionTo the residue, water was added
  5. filtrationThe solid was filtered
  6. customcollected
  7. washwashed with water thoroughly
  8. customdried

Sources & evidence

ORD record
ord-d87ea6ac89004c25a23dcf5a2dbffa31
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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