Potassium Hydroxide → HCID 18451481, compound

HRID 1270763Notes

Reaction equation

HRID 1270763 reaction equation
C(OC(=O)[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16]C(=O)C)[CH:12]=2)[C:7]=1[Cl:20])C.[OH-].[K+]>C(O)C>[Cl:20][C:7]1[C:8]2[C:13](=[CH:12][C:11]([OH:16])=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[NH2:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68804327HCID 68804327, compound

Product 1

HCID 18451481HCID 18451481, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(6-acetyloxy-1-chloro-2-naphthyl)carbamic acid ethyl ester (375 mg, 1.34 mmol) and KOH (903 mg, 16.1 mmol) in ethanol (10 mL) is heated to reflux temperature under N2 atmosphere for 4.5 hours. The reaction mixture is concentrated by rotary evaporator under high vacuum. The residual oil is partitioned between EtOAc and water. After acidification (2 N HCl), the organic layer is separated, washed with brine and dried (MgSO4). Concentration by rotary evaporator gives 1-chloro-2-amino-6-naphthol as a brown solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature under N2 atmosphere for 4.5 hours
  3. concentrationThe reaction mixture is concentrated by rotary evaporator under high vacuum
  4. customThe residual oil is partitioned between EtOAc and water
  5. customAfter acidification (2 N HCl), the organic layer is separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationConcentration
  9. customby rotary evaporator

Sources & evidence

ORD record
ord-365afdb2b5404602b96f2812f7729d22
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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