Sodium Hydroxide → 5-Chloronaphthalen-1-amine

HRID 1441789Notes

Reaction equation

HRID 1441789 reaction equation
[NH:1]([C:5]1[C:14]2[C:9](=[C:10]([Cl:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)C(C)=O.[OH-].[Na+]>CCO>[NH2:1][C:5]1[C:14]2[C:9](=[C:10]([Cl:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218748441-Acetamino-5-chloronaphthalene

Product 1

HCID 44550535-Chloronaphthalen-1-amineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above synthesized 1-acetamino-5-chloronaphthalene (52 mg, 0.24 mmol) in 3 mL EtOH was heated to reflux and treated with 0.5 mL 40% aqueous NaOH solution. The mixture was refluxed until no more starting material could be detected, cooled and concentrated under reduced pressure. The residue was taken up in CH2Cl2 (50 mL) and was washed with H2O (25 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to leave 41 mg (98%) of compound 213A as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed until
  4. temperaturecooled
  5. concentrationconcentrated under reduced pressure
  6. washwas washed with H2O (25 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36676154c98e4d0089e339b673e1e3b5
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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