Triethylamine → HCID 178484456, compound

HRID 2236710Notes

Reaction equation

HRID 2236710 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.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:28])[CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=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:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]([CH2:25][CH2:26][OH:27])[CH3:28])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 136283162-[(4-Aminophenyl)(methyl)amino]ethan-1-olHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178484456HCID 178484456, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.17 g, 0.61 mmol) and 2-[(4-amino-phenyl)-methyl-amino]-ethanol (0.10 g, 0.61 mmol) were stirred in N,N-dimethylformamide (3 mL) and triethylamine (0.16 mL) at 60-70° 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-hydroxyethyl)(methyl)amino]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (0.16 g, 64%) as a rust colored powder.

Workup

  1. customat 60-70° 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-d19e2b23127f4814be88a05b0b17d380
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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