Potassium Hydroxide → 3-Chloronaphthalen-2-amine

HRID 1270746Notes

Reaction equation

HRID 1270746 reaction equation
C(OC(=O)[NH:5][C:6]1[C:15]([Cl:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)C.[OH-].[K+]>CCO>[Cl:16][C:15]1[C:6]([NH2:5])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13463001HCID 13463001, compound

Product 1

HCID 134630023-Chloronaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.94 g (11.77 mmol) of N-(3-chloro-2-naphthyl)carbamic acid ethyl ester, and 7.93 g (141.2 mmol) KOH in 80 mL of EtOH is heated to reflux for 7 hours under an atmosphere of nitrogen. After cooling to room temperature, the solvent is evaporated in vacuo giving a residue to which ice is added. The mixture is extracted 3 times with 30 mL of CH2Cl2. The combined organic layers are dried over Na2SO4 and the solvents evaporated to give 3-chloro-2-aminonaphthalene as a brown solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 7 hours under an atmosphere of nitrogen
  3. customthe solvent is evaporated in vacuo
  4. customgiving a residue to which ice
  5. additionis added
  6. extractionThe mixture is extracted 3 times with 30 mL of CH2Cl2
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. customthe solvents evaporated

Sources & evidence

ORD record
ord-3ddce8ad3a674abfb258bdfa2c6a8d94
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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