Ammonium Hydroxide → 6,7-Dimethoxyisoquinoline-1,3(2H,4H)-dione

HRID 2236416Notes

Reaction equation

HRID 2236416 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[CH2:14][C:15]([OH:17])=O)(O)=[O:2].[NH4+:18].[OH-]>ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][C:8]=1[O:10][CH3:11])[C:1](=[O:2])[NH:18][C:15](=[O:17])[CH2:14]2

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 33079222-(carboxymethyl)-4,5-dimethoxybenzoic acid

Product 1

HCID 157656976,7-Dimethoxyisoquinoline-1,3(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 8.2 g (34.1 mmol) of 2-carboxy-4,5-dimethoxybenzeneacetic acid (Tetrahedron 1975, 31, 2607) in 17 ml of conc NH4OH is evaporated to dryness. This operation is repeated. The resulting tan solid ammonium salt is suspended in 34 ml of 1,2-dichlorobenzene. The stirred mixture is boiled in an oil bath at 210° while collecting some distillate during 90 m. The cooled mixture is stirred in hexane and H2O, and the resulting solid is collected by filtration. The white solid is stirred in satd NaHCO3 for 15 m, filtered, washed with H2O, and dried to give 3.45 g (46%), mp 234-238°; MS (ES−) m/z 220.1 (M−H)−1.

Workup

  1. customThe stirred mixture is boiled in an oil bath at 210°
  2. distillationwhile collecting some distillate during 90 m
  3. filtrationH2O, and the resulting solid is collected by filtration
  4. stirringThe white solid is stirred in satd NaHCO3 for 15 m
  5. filtrationfiltered
  6. washwashed with H2O
  7. customdried
  8. customto give 3.45 g (46%), mp 234-238°

Sources & evidence

ORD record
ord-654066b6eea64ad3979a17815538bf54
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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