Triethylamine → HCID 178483886, compound

HRID 2236723Notes

Reaction equation

HRID 2236723 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]([CH3:30])[CH2:20][CH2:21][O:22][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]([O:22][CH2:21][CH2:20][N:19]([CH3:30])[CH3:18])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68696135HCID 68696135, compound

Product 1

HCID 178483886HCID 178483886, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (70 mg, 0.25 mmol) and 4-(2-dimethylamino-ethoxy)-phenylamine hydrochloride (50 mg, 0.23 mmol) were stirred in N,N-dimethylformamide (1 mL) and triethylamine (50 μL) at 70° C. 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)ethoxy]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (81 mg, 82%).

Workup

  1. customat 70° C
  2. customThe reaction mixture is quenched by the addition of water
  3. customThe solid material is then collected
  4. washwashed with diethyl ether, water, and methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-617f512f128f42688313aa203447fc69
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…