Triethylamine → HCID 178507622, compound

HRID 2236782Notes

Reaction equation

HRID 2236782 reaction equation
[I: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.Cl.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=1[OH:28].C(N(CC)CC)C>CN(C)C=O>[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH:27]/[CH:14]=[C:5]2\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]3[C:4]\2=[CH:3][C:2]([I:1])=[CH:11][CH:10]=3)=[CH:22][C:21]=1[OH:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68698185HCID 68698185, compound

Product 1

HCID 178507622HCID 178507622, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (1.0 g, 3.0 mmol) and 2-amino-5-(aminomethyl)phenol dihydrochloride (0.64 g, 3.0 mmol) in N,N-dimethylformamide (15 mL) is added triethylamine (1.2 mL, 9.0 mmol). The mixture is stirred at room temperature for 60 hours and then concentrated to dryness under reduced pressure. The residue is then triturated with water, and the solid is collected by filtration, washed successively with diethyl ether and acetonitrile, and dried under house vacuum to provide (4Z)-4-{[(4-amino-3-hydroxybenzyl)amino]methylene}-6-iodoisoquinoline-1,3(2H,4H)-dione as a golden powder (1.3 g, 100%).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue is then triturated with water
  3. filtrationthe solid is collected by filtration
  4. washwashed successively with diethyl ether and acetonitrile
  5. customdried under house vacuum

Sources & evidence

ORD record
ord-8440e9d7d7e740d59857cdda189a7675
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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