Hydrochloric Acid → 4-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acid

HRID 717092Notes

Reaction equation

HRID 717092 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#N)=[CH:15][CH:14]=1)[NH:6][C:7]2=[O:12].[OH-:21].[Na+].Cl.[OH2:24]>>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[CH:20]=[CH:19][C:16]([C:17]([OH:24])=[O:21])=[CH:15][CH:14]=1)[NH:6][C:7]2=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 898129544-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile

Product 1

HCID 898128824-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acidYield 63%

Procedure

To 4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile (100 mg, 0.38 mmol) was added 2M NaOH (1.5 mL) and the reaction mixture irradiated using a microwave (300 W, 130° C., 20 min). The reaction mixtures was diluted with water and adjusted to pH2 with 2M HCl whereupon a pale yellow solid precipitated out of solution. The solid was filtered, washed with water and dried. The solid was dissolved in DMF and passed through a Si-thiol cartridge to remove any residual palladium, eluting with DMF. The eluent was removed in vacuo to give 4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoic acid as a pale yellow solid (120 mg, 63%).

Workup

  1. customthe reaction mixture irradiated
  2. customa microwave (300 W, 130° C., 20 min)
  3. customThe reaction mixtures
  4. customprecipitated out of solution
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried
  8. dissolutionThe solid was dissolved in DMF
  9. customto remove any residual palladium
  10. washeluting with DMF
  11. customThe eluent was removed in vacuo

Sources & evidence

ORD record
ord-3d09cb1ad1fb44f9bfcabac2baef7469
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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