Stannous Chloride → (5-Methoxynaphthalen-2-yl)hydrazine

HRID 453265Notes

Reaction equation

HRID 453265 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH3:13])[CH:3]=1.[N:14]([O-])=O.[Na+].Cl[Sn]Cl>O.Cl>[CH3:13][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([NH:1][NH2:14])=[CH:3]2

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 129927625-Methoxynaphthalen-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 66916889(5-Methoxynaphthalen-2-yl)hydrazineYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-6 °C

Procedure

To a suspension of 2-amino-5-methoxynaphthalene (3.5 g, 20 mmol) in water (65 ml) and HCl conc. (25 ml) cooled down to −6° C., sodium nitrite (1.55 g, 22 mmol) in water (15 ml) was added dropwise. It was kept at stirring, approximately at the same temperature, during 45 minutes and subsequently a solution of SnCl2 (9.3 g, 40 mmol) in HCl conc. (10 ml) was added. Once the addition was performed, it was allowed that the temperature would slowly increase until achieving room temperature, and it was filtered. The filtered solid was washed with water and ethylic ether and, subsequently, it was suspended in ethylic ether, with stirring, during a few minutes. It was filtered and dried resulting in 3.5 g of a crude brown solid, which was used directly in the following synthesis step.

Workup

  1. additionOnce the addition
  2. temperaturewould slowly increase
  3. customuntil achieving room temperature
  4. filtrationit was filtered
  5. washThe filtered solid was washed with water and ethylic ether
  6. stirringwith stirring, during a few minutes
  7. filtrationIt was filtered
  8. customdried

Sources & evidence

ORD record
ord-db901bd81fe14b859560783235d67810
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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