p-Toluenesulfonic acid → 2-Tetralone-6-carboxamide

HRID 1824296Notes

Reaction equation

HRID 1824296 reaction equation
C1O[C:4]2([CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:14]([NH2:16])=[O:15])[CH:10]=3)[CH2:5]2)[O:3]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:5]1[C:6]2[C:11](=[CH:10][C:9]([C:14]([NH2:16])=[O:15])=[CH:8][CH:7]=2)[CH2:12][CH2:13][C:4]1=[O:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 570994732-Tetralone-6-carboxamide ethylene ketal

Product 1

HCID 221477772-Tetralone-6-carboxamideYield 38.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Tetralone-6-carboxamide ethylene ketal (250 mg, 1.07 mmol) and catalytic p-toluenesulfonic acid were stirred in acetone (50 mL) at ambient temperature for 48 hours. The volatiles were removed in vacuo and the residue triturated in ethyl acetate. The solids were filtered, washed and dried to yield 77.5 mg (38%) of 2-tetralone-6-carboxamide as a white powder, pure by NMR, TLC. MS.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue triturated in ethyl acetate
  3. filtrationThe solids were filtered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-c9109dedf0374ad5907f9af7b7f3b683
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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