Stannous chloride dihydrate → HCID 55279852, compound

HRID 1696514Notes

Reaction equation

HRID 1696514 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[N:13]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl.O>[NH:1]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)[NH2:13]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 131528447-Amino-1,2,3,4-tetrahydroisoquinolin-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 55279852HCID 55279852, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 7-amino-3,4-dihydro-2H-isoquinolin-1-one (8.1 g, 50 mmol) in conc. HCl (100 mL) cooled in an ice-H2O bath was added a solution of NaNO2 (3.45 g, 50 mmol) in H2O dropwise at such a rate that the reaction mixture never rose above 5° C. After stirring for 30 min, to the resulting mixture was added a solution of SnCl2.2H2O (22.5 g, 0.1 mol) in conc. HCl (150 mL) dropwise at 0° C. in an ice-H2O bath. The resulting mixture was stirred for another 2 h at 0° C. The precipitate was collected by suction, washed with ether to afford 7-hydrazino-3,4-dihydro-2H-isoquinolin-1-one (8.3 g), which was used for the next reaction without further purification.

Workup

  1. temperaturecooled in an ice-H2O bath
  2. stirringThe resulting mixture was stirred for another 2 h at 0° C
  3. customThe precipitate was collected by suction
  4. washwashed with ether

Sources & evidence

ORD record
ord-bffe4fe48f984d439dd64af7a160509f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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