Triethylamine → HCID 178491624, compound

HRID 2236671Notes

Reaction equation

HRID 2236671 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.[OH:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:22]([NH:24][NH2:25])=[O:23].C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>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:25][NH:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:19]([OH:18])[CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dioneHCID 68694289HCID 68694289, compound

Product 1

HCID 178491624HCID 178491624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.18 g, 0.64 mmol) and 3-hydroxy-4-methoxy-benzoic acid hydrazide hydrochloride (0.18 g, 0.64 mmol) were coupled in N,N-dimethylformamide (5 mL) with triethylamine (0.30 mL) at 100° C. After cooling to room temperature and addition of 5% aqueous potassium hydrogen sulfate solution, the solid material is collected by Buchner filtration, washed with diethyl ether, water, and methanol, and then dried under house vacuum to give N′-[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]-3-hydroxy-4-methoxybenzohydrazide as a tan powder.

Workup

  1. filtrationthe solid material is collected by Buchner filtration
  2. washwashed with diethyl ether, water, and methanol
  3. customdried under house vacuum

Sources & evidence

ORD record
ord-9d1f3a5dfc874208b4e55f60bebe417f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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