p-Toluenesulfonic acid → HCID 21220547, compound

HRID 1584735Notes

Reaction equation

HRID 1584735 reaction equation
O=[C:2]1[C:11]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH:3]1[CH2:12][C:13]([O:15]C)=O.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[F:17][C:18]([F:27])([F:28])[C:19]1[CH:20]=[CH:21][C:22]([N:25]2[C:13](=[O:15])[CH2:12][CH:3]3[C:2]([C:11]4[CH:10]=[N:9][CH:8]=[CH:7][C:6]=4[CH2:5][CH2:4]3)=[N:26]2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 21220530HCID 21220530, compound

Product 1

HCID 21220547HCID 21220547, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 5,6,7,8-tetrahydro-8-oxoisoquinolin-7-acetate (1.0 g), 4-trifluoromethyl-phenylhydrazine (1.6 g) and para-toluenesulphonic acid (0.25 g) were heated under reflux in xylene (20 ml) for 4 hours. The cooled reaction was poured into 2M sodium hydroxide solution and extracted with ethyl acetate, which was then washed with brine, dried, and evaporated to a gum. The gum was chromatographed on silica gel, eluting with ethyl acetate-isohexane (1:1), to afford a solid which was crystallised from isopropanol-isohexane to yield the title compound (0.25 g),

Workup

  1. customThe cooled reaction
  2. extractionextracted with ethyl acetate, which
  3. washwas then washed with brine
  4. customdried
  5. customevaporated to a gum
  6. customThe gum was chromatographed on silica gel
  7. washeluting with ethyl acetate-isohexane (1:1)
  8. customto afford a solid which
  9. customwas crystallised from isopropanol-isohexane

Sources & evidence

ORD record
ord-3327821bc1874849aa37fa8279f4e62c
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

Loading…