Water → 3,4-Dihydroisoquinolin-7-amine

HRID 650947Notes

Reaction equation

HRID 650947 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.O.[OH-].[K+]>C(O)C.Cl>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 37512877-Nitro-3,4-dihydroisoquinoline

Product 1

HCID 114236673,4-Dihydroisoquinolin-7-amineYield 88.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

7-Nitro-3,4-dihydroisoquinoline (0.60 g, 3.4 mmol) [prepared according to the procedure of A. P. Venkov et al, Syn. Commun., 1996 26 127] was dissolved in ethanol (100 ml) and heated to 60° C. This hot solution was treated with a solution of tin (II) chloride dihydrate (3.08 g, 13.7 mmol) in conc. HCl (10 ml). The resultant mixture was heated at 60° for 1 h. Upon cooling, the reaction mixture was poured into water (100 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% conc. ammonia: 4.5% methanol: 95% dichloromethane) yielded the title compound as a dark yellow oil (0.44 g, 88%).

Workup

  1. temperatureUpon 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% conc. ammonia: 4.5% methanol: 95% dichloromethane)

Sources & evidence

ORD record
ord-ab828951a33148e586df01ae6a24cfff
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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