Iodoethane → 4-Carbomethoxy-3-ethoxy-6,7-dimethoxy-1-methylisoquinoline

HRID 1638702Notes

Reaction equation

HRID 1638702 reaction equation
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH3:19])=[N:7][C:6]=1[OH:20])([O:3][CH3:4])=[O:2].I[CH2:22][CH3:23]>CN(C)C=O.C(=O)([O-])[O-].[Ag+2]>[C:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([CH3:19])=[N:7][C:6]=1[O:20][CH2:22][CH3:23])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 178498979HCID 178498979, compound

Product 1

HCID 146261484-Carbomethoxy-3-ethoxy-6,7-dimethoxy-1-methylisoquinoline

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A slurry of 4-carbomethoxy-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline (0.500 g, 1.81 mmol) and silver carbonate (0.498 g, 1.81 mmol) in dimethylformamide (15 mL) was stirred for 20 minutes and then iodoethane (0.326 g, 2.09 mmol) was added and the slurry was stirred at room temperature for two days. The silver iodide precipitate was filtered off and the filtrate was diluted with water (75 mL) and extracted with ether (3×40 mL). The ether was successively washed with water and saturated sodium chloride solution and dried (Na2SO4). The ether was evaporated in vacuo and the solid residue was triturated with ether/hexane to give the title compound (310 mg, 56% as a pale yellow solid, mp 147°-149° C. IR (KBr): 1709, 1629, 1572 cm-1. NMR (CDCl3): δ 1.40 (t, 3H, 4-OCH2CH3), 2.80 (s, 3H, 1-CH3), 3.98 (s, 9H, 6,7-Ar-OCH3 and 4-COOCH3); 4.50 (q, 2H, 4-OCH2CH3); MS: 305 (M+).

Workup

  1. filtrationThe silver iodide precipitate was filtered off
  2. additionthe filtrate was diluted with water (75 mL)
  3. extractionextracted with ether (3×40 mL)
  4. washThe ether was successively washed with water and saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customThe ether was evaporated in vacuo
  7. customthe solid residue was triturated with ether/hexane

Sources & evidence

ORD record
ord-239393f395cd4ecbb2bb17bc16fe26eb
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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