Water → 6-Methoxy-3-methylisoquinolin-1(2H)-one

HRID 606309Notes

Reaction equation

HRID 606309 reaction equation
[C:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=O)[O:6]C1=O)(=O)[CH3:2].O.[NH4+:19].[OH-]>>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:6])[NH:19][C:1]([CH3:2])=[CH:4]2

Participants

4

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 578931304-Acetyl-6-methoxy-1H-2-benzopyran-1,3(4H)-dione

Product 1

HCID 123270606-Methoxy-3-methylisoquinolin-1(2H)-one

Conditions

Temperature
100 °C

Procedure

A suspension of 4-acetyl-6-methoxy-isochroman-1,3-dione (10 g, 43 mmol) in NH4OH (60 ml) in a pressure vessel is heated for 2 h at 100° C. After cooling, the reaction mixture is poured into water. The white solid is filtered, washed with water, and dried to give 6.7 g of 6-methoxy-3-methyl-2H-isoquinolin-1-one. 1H NMR (CDCl3) 11.0 (br s, 1H), 8.28 (d, 1H), 6.98 (d, 1H), 6.81 (s, 1H), 6.23 (s, 1H), 3.89 (s, 3H), 2.37 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe white solid is filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3c4e933419ef440f829450bc5df37786
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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