Water → HCID 11126561, compound

HRID 650951Notes

Reaction equation

HRID 650951 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[CH2:5][CH2:4][N:3]=1.O.O.[Sn](Cl)Cl.O.[OH-].[K+]>C(O)C.Cl>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][N:3]=[C:2]2[CH3:1])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 109322281-Methyl-7-nitro-3,4-dihydroisoquinoline

Product 1

HCID 11126561HCID 11126561, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

(±) 1-Methyl-7-nitro-3,4-dihydroisoquinoline (2.0 g, 10.5 mmol) was dissolved in ethanol (150 ml) and heated to 60° C., before treatment with a solution of tin (II) chloride dihydrate (9.5 g, 42.1 mmol) in conc. HCl (30 ml). The resultant mixture was heated at 60° C. for 1 h. After cooling, the reaction mixture was poured into water (200 ml) and basified (pH 9) with KOH pellets, liberating an oily residue. This residue was extracted into dichloromethane and dried over magnesium sulfate. Purification by chromatography through silica gel, eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) yielded the title compound as a dark brown oil (0.93 g, 55%).

Workup

  1. temperatureAfter cooling
  2. extractionThis residue was extracted into dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. customPurification by chromatography through silica gel
  5. washeluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2)

Sources & evidence

ORD record
ord-2da4d7be1b6b494586c4894f7ac53089
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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