Triethylamine → HCID 178490302, compound

HRID 2236664Notes

Reaction equation

HRID 2236664 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.[NH2:18][CH:19]([C:21]1[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[C:25]([OH:27])[CH:26]=1)[CH3:20].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:18][CH:19]([C:21]1[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[C:25]([OH:27])[CH:26]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42625429HCID 42625429, compoundHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178490302HCID 178490302, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.10 g, 0.35 mmol) and 5-(1-amino-ethyl)-2-methoxyphenol hydrochloride (excess) were coupled in N,N-dimethylformamide (2 mL) with triethylamine (0.15 mL). The solid material is collected by Buchner filtration, washed with diethyl ether and acetonitrile, and then dried under house vacuum to give (4Z)-6-bromo-4-({[1-(3-hydroxy-4-methoxyphenyl)ethyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione as a light tan powder (0.11 g, 73%).

Workup

  1. filtrationThe solid material is collected by Buchner filtration
  2. washwashed with diethyl ether and acetonitrile
  3. customdried under house vacuum

Sources & evidence

ORD record
ord-425a25f4632a449eab243192da7dd0aa
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…