Methanol → isoquinolin-5(1 H)-one

HRID 1605264Notes

Reaction equation

HRID 1605264 reaction equation
[Na].Cl.CO[C:5]([C:7]1[C:8]2[C:9](CN)=[CH:10][NH:11][C:12]=2[CH:13]=[CH:14][CH:15]=1)=O.C[OH:19]>>[CH2:5]1[C:7]2[C:8]([C:12](=[O:19])[CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:10]=[N:11]1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 179257783-(Aminomethyl)indole-4-carboxylic acid methyl ester hydrochloride

Product 1

HCID 22598424isoquinolin-5(1 H)-one

Procedure

Sodium metal (19.2 g) is dissolved in absolute methanol (1 l.) with ice-water cooling. To the clear solution is added a solution of 3-(aminomethyl)indole-4-carboxylic acid methyl ester hydrochloride (102.7 g), described in Example 3, in absolute methanol (1 l.). The addition is done in portions within a few minutes. After stiring for 1.5 hr at room temperature the solution is concentrated to near dryness and ice cold water (250 ml) is added to the crystalline residue. The precipitate is collected, washed with cold water and dried to give the title compound, mp. 232°-234°C, identical to the product of Preparation A of this example.

Workup

  1. additionThe addition
  2. waitis done in portions within a few minutes
  3. concentrationthe solution is concentrated
  4. additionis added to the crystalline residue
  5. customThe precipitate is collected
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-001ac6d9b41e4af2b4e7128b000d2ed7
Source dataset
uspto-grants-1976_04
Patent number
US03950343

Reaction notes

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