Triethylamine → HCID 178483764, compound

HRID 2236694Notes

Reaction equation

HRID 2236694 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.[CH3:18][N:19]([CH3:31])[CH2:20][CH2:21][N:22]([CH3:30])[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.C(N(CC)CC)C>CN(C)C=O>[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:29][C:26]1[CH:25]=[CH:24][C:23]([N:22]([CH2:21][CH2:20][N:19]([CH3:31])[CH3:18])[CH3:30])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68696409HCID 68696409, compound

Product 1

HCID 178483764HCID 178483764, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.28 g, 1.0 mmol) and N-[2-(dimethylamino)ethyl]-N-methylbenzene-1,4-diamine hydrochloride (0.30 g, 1.0 mmol) were stirred in N,N-dimethylformamide (5 mL) with triethylamine (0.6 mL). The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with diethyl ether, water, and methanol and then dried under vacuum to give (4Z)-6-bromo-4-[({4-[[2-(dimethylamino)ethyl](methyl)amino]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (0.24 g, 55%) as a golden powder.

Workup

  1. customThe reaction mixture is quenched by the addition of water
  2. customThe solid material is then collected
  3. washwashed with diethyl ether, water, and methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0d8ee3d06fc04b10b27ebc24277c2d69
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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