2-Methoxy-5-[(methylamino)methyl]phenol → (4Z)-6-bromo-4-{[(3-hydroxy-4-methoxybenzyl)(methyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione

HRID 2236639Notes

Reaction equation

HRID 2236639 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH3:27])=[CH:21][C:20]=1[OH:28]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[N:26]([CH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([OH:28])[CH:21]=1)[CH3:27]

Participants

4

Reactant 2

HCID 15199372-Methoxy-5-[(methylamino)methyl]phenolHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 42625518(4Z)-6-bromo-4-{[(3-hydroxy-4-methoxybenzyl)(methyl)amino]methylene}isoquinoline-1,3(2H,4H)-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4E)-6-Bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.15 g, 0.53 mmol) and 2-methoxy-5-methylaminomethyl-phenol (80 mg, 0.48 mmol) were stirred in tetrahydrofuran (10 mL) at room temperature. The reaction mixture is concentrated under reduced pressure. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-{[(3-hydroxy-4-methoxybenzyl)(methyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione as a yellow solid (0.19 g, 95%).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe solid material is then collected
  3. washwashed with diethyl ether, water, and methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a0d916b536804624a7cca8fce0f46ee8
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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