Sodium Hydroxide → isoquinolin-5(1 H)-one

HRID 1605263Notes

Reaction equation

HRID 1605263 reaction equation
CO[C:3](=NO)[C:4]1[C:5]2[C:6](C=O)=[CH:7][NH:8][C:9]=2[CH:10]=[CH:11][CH:12]=1.[H][H].C[O:20]C(C1C2C(CN)=CNC=2C=CC=1)=O.[OH-].[Na+]>C(O)(=O)C.O.[Pt]=O>[CH2:3]1[C:4]2[C:5]([C:9](=[O:20])[CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:7]=[N:8]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 17925779methyl 3-(aminomethyl)-1H-indole-4-carboxylateHCID 867332223-Formylindole-4-carboxylic acid methyl ester oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 22598424isoquinolin-5(1 H)-one

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 3-formylindole -4 -carboxylic acid methyl ester oxime (1.6 g), described in Example 2 and platinum oxide (120 mg) in 60 ml of acetic acid is stirred in a hydrogen atmosphere for 16 hr. Removal of the catalyst and concentration of the solution affords an oily residue [the acetic acid addition salt of 3-(aminomethyl)indole -4-carboxylic acid methyl ester] . The oil is suspended in water. The mixture is rendered alkaline with 10% NaOH. The solid is collected, triturated with 30% acetone in benzene and recrystallized from ethanol to afford the title compound, mp. 232°-234°C, νmaxCHCl3 1668 cm-1.

Workup

  1. customRemoval of the catalyst and concentration of the solution
  2. customaffords an oily residue [
  3. customThe solid is collected
  4. customtriturated with 30% acetone in benzene
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-84441f125e534acebb1d107bc2e9c858
Source dataset
uspto-grants-1976_04
Patent number
US03950343

Reaction notes

Loading…