Sodium Hydroxide → HCID 14625300, compound

HRID 1638996Notes

Reaction equation

HRID 1638996 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][N:14]([C:21](=[N:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[CH:26][C:25]=1[C:34]#[N:35])[CH3:22])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(N(C)C)=O.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].O>[NH2:35][C:34]1[C:25]2[C:24](=[CH:29][C:28]([O:30][CH3:31])=[C:27]([O:32][CH3:33])[CH:26]=2)[N:23]=[C:21]([N:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH2:15]2)[CH:22]=1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 31374DimethylacetamideHCID 14625298HCID 14625298, compound

Product 1

HCID 14625300HCID 14625300, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

N-(1-[6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2-yl]ethylidene)-2-cyano-4,5-dimethoxyaniline (10.92 g), anhydrous zinc chloride (3.16 g) and dimethylacetamide (25 ml) were mixed at 20° and then stirred at reflux for two hours. The reaction mixture was allowed to cool to about 40° and then 2N sodium hydroxide (16 ml) was added. The mixture was cooled to 25° and stirred for fifteen mixtures. 2N Sodium hydroxide (10 ml) and water (50 ml) were added and the reaction mixture was then extracted with methylene chloride (3×100 ml). The combined organic extracts were washed (H2O), dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica (Merck "Art.9385") under medium pressure eluting with methylene chloride containing gradually increasing amounts (1-20%) of methanol. The combined product-containing fractions were evaporated and the residue was recrystallised from ethanol and washed (Et2O) to give 4-amino-2-(6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2-yl)-6,7-dimethoxyquinoline (7.1 g) as a pale yellow powder, m.p. 181°-2°.

Workup

  1. temperatureat reflux for two hours
  2. temperatureto cool to about 40°
  3. temperatureThe mixture was cooled to 25°
  4. stirringstirred for fifteen mixtures
  5. extractionthe reaction mixture was then extracted with methylene chloride (3×100 ml)
  6. washThe combined organic extracts were washed (H2O)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica (Merck "Art.9385") under medium pressure
  10. washeluting with methylene chloride containing gradually increasing amounts (1-20%) of methanol
  11. additionThe combined product-containing fractions
  12. customwere evaporated
  13. customthe residue was recrystallised from ethanol
  14. washwashed (Et2O)

Sources & evidence

ORD record
ord-204e57e8d77e4421970f4c27a7241bfc
Source dataset
uspto-grants-1989_11
Patent number
US04882337

Reaction notes

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