Sodium Hydroxide → 2,7-Naphthalenediamine

HRID 990314Notes

Reaction equation

HRID 990314 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.[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

5

Reactant 3

HCID 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 HCA 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-646edf957eb44f028e09322c7314046e
Source dataset
uspto-grants-2002_10
Patent number
US06458998B1

Reaction notes

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