Stannous chloride dihydrate → 6-Hydrazinoindan-1-one

HRID 1696494Notes

Reaction equation

HRID 1696494 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[N:12]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[NH:1]([C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[NH2:12]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 3128956-amino-2,3-dihydro-1H-inden-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 552812116-Hydrazinoindan-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a mixture of 6-aminoindan-1-one (7.2 g, 11.8 mmol) in conc. HCl (20 mL) at 0° C. was added dropwise an aqueous solution of NaNO2 (0.9 g, 13 mmol). After 30 min, a solution of SnCl2.2H2O (5.9 g, 26.2 mmol) in conc. HCl was added dropwise at such a rate that the reaction temperature never rose above 5° C. After the addition was completed, the mixture was stirred at RT for 2 h. The mixture was extracted with Et2O to afford 6-hydrazinoindan-1-one. MS (ESI) m/z: 199 (M+H+).

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with Et2O

Sources & evidence

ORD record
ord-47d571bfbcf4484ba0628cf177945c0f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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