Tryptamine → HCID 178518284, compound

HRID 2236599Notes

Reaction equation

HRID 2236599 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][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1>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][CH2:18][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518284HCID 178518284, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (124.5 mg, 0.44 mmol), tryptamine (70.7 mg, 0.44 mmol) in 1 mL of N,N-dimethylformamide is heated at 110° C. for 1.5 h. After cooling in the refrigerator, the precipitate is collected, and washed with ether to give 100 mg (55%) of yellow solid mp 278-280° C.; HRMS (ESI) m/z calcd for C20H16BrN3O2 408.03531. found 408.03493 (M+H)+1, Analysis for C20H16BrN3O2; Calcd: C, 58.55; H, 3.93; N, 10.24. Found: C, 58.34; H, 3.63; N, 10.21.

Workup

  1. temperatureAfter cooling in the refrigerator
  2. customthe precipitate is collected
  3. washwashed with ether

Sources & evidence

ORD record
ord-f3320f71e32a4cce8e4d52a74d2c67b7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…