Water → 5,10-Dihydro-7,8-dimethoxyimidazo[1,2-b]isoquinoline

HRID 857864Notes

Reaction equation

HRID 857864 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:13]=1[CH2:12][C:11]1[CH:10]=[C:9](O)[C:8]([OH:15])=[CH:7][C:6]=1[CH2:5]2.[C:16]([O-:19])([O-])=O.[K+].[K+].O.[CH3:23]N(C=O)C>[Cl-].C1([N+](C)(C)C)C=CC=CC=1>[CH3:23][O:15][C:8]1[C:9]([O:19][CH3:16])=[CH:10][C:11]2[CH2:12][C:13]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH2:5][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 219902425,10-Dihydroimidazo[1,2-b]isoquinoline-7,8-diol

Product 1

HCID 219901985,10-Dihydro-7,8-dimethoxyimidazo[1,2-b]isoquinolineYield 8.4%

Reagents, catalysts & solvents 1

HCID 67309Phenyltrimethylammonium chlorideCatalyst

Procedure

A mixture of 5,10-dihydro-imidazo[1,2-b]isoquinoline-7,8-diol, obtained according to the procedure described in Ex.No. A8c, (0.155 mol), phenyltrimethylammonium chloride (0.31 mol) and K2CO3 (0.68 mol) in DMF (400 ml) was stirred at 90° C. for 20 hours, cooled, poured out into H2O and filtered over dicalite. The filtrate was separated into its layers. The organic layer was washed with H2O, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 100/0 to 97/3). The pure fractions were collected and the solvent was evaporated, yielding 3 g of 5,10-dihydro-7,8-dimethoxyimidazo[1,2-b]isoquinoline (8.4%) (interm. 22).

Workup

  1. customobtained
  2. temperaturecooled
  3. filtrationfiltered over dicalite
  4. customThe filtrate was separated into its layers
  5. washThe organic layer was washed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified over silica gel on a glass
  10. filtrationfilter (eluent: CH2Cl2/CH3OH 100/0 to 97/3)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bdb3d2557df3483ea49c1d79a50094d8
Source dataset
uspto-grants-2006_12
Patent number
US07148214B1

Reaction notes

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