Hydrochloric Acid → 2,7-Naphthalenediamine

HRID 1791076Notes

Reaction equation

HRID 1791076 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[CH:9][CH:10]=2)[CH:5]=1)([O-])=O.Cl.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([NH2:14])[CH:7]=2)[CH:12]=[CH:13][C:4]=1[NH2:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 906202,7-Dinitronaphthalene

Product 1

HCID 119512,7-Naphthalenediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.39 g (6.37 mmol) of 2,7-dinitronaphthalene (124) was added 25 mL of concentrated HCl and 15 mL of ethanol. Then, 9.6 g (50.9 mmol) of tin (II) chloride was added and the reaction was heated at 78 C for 24 hours. The reaction was made basic with NaOH and extracted with ethyl acetate. The ethyl acetate layer was dried (MgSO4), filtered, and the volatiles removed by rotary evaporation. The product was purified by silica gel column chromatography eluting with 1% methanol in dichloromethane. This provided 0.965 g of compound 125.

Workup

  1. temperaturethe reaction was heated at 78 C for 24 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe volatiles removed by rotary evaporation
  6. customThe product was purified by silica gel column chromatography
  7. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-f09e7bbc3f314d7ea743e1a38425437f
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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