Water → 8,9-Dimethoxychromeno[4,3,2-de]isoquinoline

HRID 895401Notes

Reaction equation

HRID 895401 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[N+]([O-])=O)[CH:14]=[N:13][CH:12]=2)[C:4]=1[OH:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]2[O:24][C:19]3[C:20]4[C:15]([CH:16]=[CH:17][CH:18]=3)=[CH:14][N:13]=[CH:12][C:11]=4[C:5]=2[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 129719202,3-Dimethoxy-6-(5-nitroisoquinolin-4-yl)phenol

Product 1

HCID 129719218,9-Dimethoxychromeno[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Phenol 5a (4.65 g, 0.014 mol) was dissolved in 100 ml of dry N,N-dimethylformamide. The solution was degassed with argon for thirty minutes. Potassium carbonate (5.80 g, 0.042 mol) was added to the yellow solution in one portion. After heating at 80° C. for one hour, the mixture had turned brown and no more starting material remained. After the solution was cooled to room temperature, 200 ml of water was added. The aqueous layer was extracted with dichloromethane (3×500 ml), this organic extract was washed with water (3×500 ml), dried (Na2SO4), and concentrated. A white powder (3.65 g 92%) was obtained that was used in the next reaction without further purification. An analytical sample was recrystallized from ethyl acetate:hexane: mp 195-196° C.; 1H NMR: (300 MHz, CDCl3): 9.02 (s, 1H); 8.82 (s, 1H); 7.87 (d, 1H, J=8.7 Hz); 7.62 (m, 3H); 7.32 (dd, 1H, J=6.0, 1.5 Hz); 6.95 (d, J=9.6 Hz); 3.88 (s, 3H); 3.82 (s, 3H). CIMS m/z: 280 (M+H+, 100%).

Workup

  1. customThe solution was degassed with argon for thirty minutes
  2. temperatureAfter the solution was cooled to room temperature
  3. extractionThe aqueous layer was extracted with dichloromethane (3×500 ml)
  4. extractionthis organic extract
  5. washwas washed with water (3×500 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customA white powder (3.65 g 92%) was obtained
  9. customthat was used in the next reaction without further purification
  10. customAn analytical sample was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a967a72efd074dafa4b1ef97e9edf67f
Source dataset
uspto-grants-2005_07
Patent number
US06916823B2

Reaction notes

Loading…