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

HRID 1167353Notes

Reaction equation

HRID 1167353 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-bc06dde8dfe848608e62e2dd8cd69bb1
Source dataset
uspto-grants-2003_09
Patent number
US06617347B1

Reaction notes

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