Lithium hydroxide, monohydrate → HCID 18451488, compound

HRID 1270751Notes

Reaction equation

HRID 1270751 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)[C:7]=1[F:17])C.O[Li].O>CCO.O>[F:17][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:15]([Cl:16])[C:6]=1[NH2:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68805719HCID 68805719, compound

Product 1

HCID 18451488HCID 18451488, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1.43 g (5.34 mmol) of N-(1-fluoro-3-chloro-2-naphthyl)carbamic acid ethyl ester, and 4.48 g (106.8 mmol) LiOH.H2O in 30 mL of EtOH and 70 mL of H2O is heated to reflux for 16 hours under an atmosphere of nitrogen. After cooling to room temperature, the mixture is concentrated in vacuo to give a residue that is extracted 3 times with 30 mL CH2Cl2. The combined organic layers are washed with 30 mL of saturated aqueous NaHCO3, 30 mL of saturated brine, dried over MgSO4 and the solvents evaporated to give 1-fluoro-3-chloro-2-aminonaphthalene as a brown solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 16 hours under an atmosphere of nitrogen
  3. concentrationthe mixture is concentrated in vacuo
  4. customto give a residue that
  5. extractionis extracted 3 times with 30 mL CH2Cl2
  6. washThe combined organic layers are washed with 30 mL of saturated aqueous NaHCO3, 30 mL of saturated brine
  7. dry with materialdried over MgSO4
  8. customthe solvents evaporated

Sources & evidence

ORD record
ord-1043efe567ee49b991075ab61bd5b252
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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