Sodium Hydroxide → 4-Amino-1-naphthaldehyde

HRID 1166788Notes

Reaction equation

HRID 1166788 reaction equation
[S].[N+:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH3:15])=[CH:7][CH:6]=1)([O-])=O.[OH-:16].[Na+]>C(O)C.C(OCC)(=O)C>[NH2:2][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:16])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 701554-Methyl-1-nitronaphthaleneHCID 5362487Sulfur

Product 1

HCID 229991604-Amino-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring boiling solution of sulfur (3.7 g) in 12% aqueous NaOH (50 mL) was added a solution of 4-nitro-1-methylnaphthalene (8 g) in ethanol (50 mL). After refluxing the solution for one hour, the reaction was diluted with 500 mL of ethyl acetate and washed with water and brine, dried over MgSO4, and concentrated. The product was purified via silica gel column chromatography using ethyl acetate:hexane (5:95 to 10:90). The product (2.54 g, 34%) was stored at −78° C.

Workup

  1. temperatureAfter refluxing the solution for one hour
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified via silica gel column chromatography
  6. customwas stored at −78° C.

Sources & evidence

ORD record
ord-8d668a3fd8f045c186ceef8d2ef27b55
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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