Triethylamine → HCID 178491077, compound

HRID 2236658Notes

Reaction equation

HRID 2236658 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.Cl.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:22][NH2:23].C(N(CC)CC)C>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]\[NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:19]([F:18])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22467403247570-27-0HCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178491077HCID 178491077, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.11 g, 0.39 mmol) and 3-fluoro-4-methoxy-benzylamine hydrochloride (75 mg, 0.39 mmol) in tetrahydrofuran (5 mL) is added triethylamine (0.13 mL, 0.98 mmol). After 15 minutes of stirring, the solvent is evaporated under reduced pressure. The solid material is collected by Buchner filtration, washed successively with diethyl ether, water, and methanol, and then dried under house vacuum to give (4Z)-6-bromo-4-{[(3-fluoro-4-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione as an off-white solid (0.11 g, 69%).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. filtrationThe solid material is collected by Buchner filtration
  3. washwashed successively with diethyl ether, water, and methanol
  4. customdried under house vacuum

Sources & evidence

ORD record
ord-830bcfec633b462e93f018e3782ea4b1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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