Lithium Hydroxide → HCID 24075694, compound

HRID 1950802Notes

Reaction equation

HRID 1950802 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][NH:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Li+]>CN(C=O)C.O.C1COCC1>[CH:18]1([N:17]([CH3:16])[C:2]2[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 7514N-MethylcyclohexylamineHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 24075694HCID 24075694, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 4-fluoro-3-nitrobenzoate (Chontech 01072; 500 mg; 2.35 mmol; 1 eq.) and N-methylcyclohexylamine (Aldrich 10,332-2; 796.59 mg; 7.04 mmol; 3 eq.) in DMF (2 mL) was stirred at 50° C. for 3 hours. The reaction was then allowed to return to room temperature and diluted with water. Extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo gave a yellow oil. The oil was taken up in THF (15 mL) and lithium hydroxide (280.86 mg; 11.73 mmol; 5 eq.) was added followed by water (15 mL). The reaction mixture was stirred at room temperature for 5 hours. After evaporation of the solvent, the solution was diluted with water and washed with Et2O. The aqueous layer was acidified to pH 4 with AcOH, extracted with Et2O, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a yellow solid.

Workup

  1. customto return to room temperature
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying over sodium sulfate and concentration in vacuo
  4. customgave a yellow oil
  5. stirringThe reaction mixture was stirred at room temperature for 5 hours
  6. customAfter evaporation of the solvent
  7. additionthe solution was diluted with water
  8. washwashed with Et2O
  9. extractionextracted with Et2O
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a825f94b4d04222b9c6fceb19d46ae2
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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