p-Toluenesulfonic acid monohydrate → Ethyl 3-acetamido-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate

HRID 2220741Notes

Reaction equation

HRID 2220741 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([NH:19][C:20](=[O:22])[CH3:21])([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])[C:6](OCC)=[O:7])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:1]([O:3][C:4]([C:5]1([NH:19][C:20](=[O:22])[CH3:21])[CH2:11][C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:18][C:6]1=[O:7])=[O:23])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59773563HCID 59773563, compound

Product 1

HCID 21853904Ethyl 3-acetamido-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.0 eq. of 80 and 0.3 eq of p-toluenesulfonic acid hydrate in EtOH was refluxed for 2 hrs. The mixture was then stirred at rt for a time sufficient for reaction completion. After rotary evaporation, 100 mL of saturated aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic extracts were dried over MgSO4 and vacuum filtered. The filtrate was rotary evaporated and dried under vacuum to yield 81.

Workup

  1. customAfter rotary evaporation, 100 mL of saturated aqueous NaHCO3
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4 and vacuum
  5. filtrationfiltered
  6. customThe filtrate was rotary evaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6b6cd9f0470a4ad58c2e29d7b2c89266
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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