5-Amino-2-naphthol → HCID 67519936, compound

HRID 2115800Notes

Reaction equation

HRID 2115800 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([OH:12])=[CH:7]2.[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=1>CN(C=O)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:12][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=1)=[CH:7]2

Participants

6

Reactant 3

HCID 68655-Amino-2-naphtholHCID 24758Sodium hydrideHCID 14768144-Chloro-N-methylpicolinamide

Product 1

HCID 67519936HCID 67519936, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-amino-2-napthol (2.8 g, 17.6 mmol) in DMF (20 mL), NaH (60% in oil, 843 mg, 21.1 mmol) was added and stirred until the bubbling stopped. To the mixture 4-chloro-N-methylpicolinamide (Org. Proc. Res. & Dev., 2002, 6, 777-781)(1 g, 5.86 mmol) was added and the reaction heated to 90° C. for 22 h. The mixture was cooled to RT and diluted with CHCl3 and washed with water. The emulsion was filtered thru a pad of Celite and the layers separated. The water was washed with CHCl3 and the organic portions combined and washed with 1N NaOH and brine, dried with Na2SO4, filtered and evaporated. The residue was purified by column chromatography using hexanes and EtOAc as the eluent to give the title compound as a rose-colored solid.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with water
  3. filtrationThe emulsion was filtered
  4. customthe layers separated
  5. washThe water was washed with CHCl3
  6. washwashed with 1N NaOH and brine
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-37d772909ad946e9a2115e9e0d53ea99
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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