Triethylamine → HCID 178467981, compound

HRID 2236636Notes

Reaction equation

HRID 2236636 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][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:23]([OH:25])[CH:24]=1.[CH2:31](N(CC)CC)C>CN(C=O)C>[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][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])=[C:23]([OH:25])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 426255215-(Aminomethyl)-2-(2-methoxyethoxy)phenolHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178467981HCID 178467981, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.40 g, 1.42 mmol) in 5 mL of N,N′-dimethylformamide is added 5-(aminomethyl)-2-(2-methoxyethoxy)phenol (0.33 g, 1.70 mmol) and 0.44 mL (4.26 mmol) of triethylamine. The reaction mixture is heated at room temperature overnight under N2. Mass spectroscopy suggested the completion of reaction. Reaction mixture is subsequently evaporated under high-pressure vacuum to brown solid. The solid is stirred in 5 mL of methanol for 10 min, then filtered, and washed in turn with 100 mL of water, 100 mL of methanol, and ether and hexane to afford 0.48 g (76.2% yield) of tan solid: mp 179-180° C.; MS (ESI) m/z 447.0-449.0 (M+H)+1

Workup

  1. customthe completion of reaction
  2. customReaction mixture
  3. customis subsequently evaporated under high-pressure vacuum to brown solid
  4. filtrationfiltered
  5. washwashed in turn with 100 mL of water, 100 mL of methanol, and ether and hexane

Sources & evidence

ORD record
ord-dcff150d0f46479ba7c5adc48d3899ca
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…