p-Toluenesulfonic acid → HCID 68988088, compound

HRID 69419Notes

Reaction equation

HRID 69419 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]3[CH2:31][CH2:30][C:25]4(OCC[O:26]4)[CH2:24]3)=[CH:19][CH:18]=1)[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]3[CH2:31][CH2:30][C:25](=[O:26])[CH2:24]3)=[CH:19][CH:18]=1)[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 689920606-butoxy-2-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)phenyl]-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 68988088HCID 68988088, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-butoxy-2-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)phenyl]-3,4-dihydro-2H-isoquinolin-1-one (1.40 g), p-toluenesulfonic acid (57 mg) and acetone (40 mL) was boiled under reflux for 12 hours and then concentrated. The residue was partitioned between sodium carbonate solution and ethyl acetate. The organic phase was dried and concentrated. The product with the molecular weight of 378.48 (C23H26N2O3) was obtained in this way; MS (ESI): 379 (M+H+).

Workup

  1. temperatureunder reflux for 12 hours
  2. concentrationconcentrated
  3. customThe residue was partitioned between sodium carbonate solution and ethyl acetate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product with the molecular weight of 378.48 (C23H26N2O3) was obtained in this way

Sources & evidence

ORD record
ord-6dfa129263f14983beed32c30c97c363
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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