6-Aminoquinoline → HCID 178518337, compound

HRID 2236735Notes

Reaction equation

HRID 2236735 reaction equation
[I: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:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2>CN(C)C=O>[I: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]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2

Participants

4

Reactant 2

HCID 113736-AminoquinolineHCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518337HCID 178518337, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-iodo-4-methoxymethylene-4H-isoquinoline-1,3-dione (164.5 mg, 0.5 mmol), 6-aminoquinoline (72.2 mg, 0.5 mmol) in 1 mL of N,N-dimethylformamide is heated at 110° C. for 0.5 h. After cooling in the refrigerator, the precipitate is collected, and washed with N,N-dimethylformamide (DMF) and ether to give 189 mg (85%) of yellow solid. MS (ESI) m/z 442.0 (M+H)+1

Workup

  1. temperatureAfter cooling in the refrigerator
  2. customthe precipitate is collected
  3. washwashed with N,N-dimethylformamide (DMF) and ether

Sources & evidence

ORD record
ord-003422fad776468498c0f6081e24711c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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