Lithium hydroxide, monohydrate → HCID 69331671, compound

HRID 1241480Notes

Reaction equation

HRID 1241480 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10]C(=O)C(F)(F)F)[CH3:9])=[C:4]([N+:17]([O-:19])=[O:18])[C:3]=1[F:20].O.[OH-].[Li+]>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[C:4]([N+:17]([O-:19])=[O:18])[C:3]=1[F:20]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 21934756HCID 21934756, compound

Product 1

HCID 69331671HCID 69331671, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[1-(4-Chloro-3-fluoro-2-nitro-phenyl)-ethyl]-2,2,2-trifluoro-acetamide (286 mg, 0.909 mmol) was dissolved at room temperature in THF (10 mL). Then, a solution of lithium hydroxide monohydrate (46 mg, 1.09 mmol) in water (2 mL) was added. The reaction was followed by TLC, using ethyl acetate as solvent. After 2 h., more lithium hydroxide monohydrate (46 mg, 1.09 mmol) in water (2 mL) was added. The reaction was stirred at room temperature for three days. Then, the reaction was extracted with ethyl acetate-sodium hydroxide (1N) and brine. The organic layer was collected, dried with sodium sulfate, filtered and concentrated under vacuum to produce a crude, which it was chromatograph over silica gel to yield 148 mg of 1-(4-chloro-3-fluoro-2-nitro-phenyl)-ethylamine. 1H NMR (400 MHz, Cl3CD) δ 7.90 (d, J=6.43 Hz, 1H), 7.64 (d, J=10.07 Hz, 1H), 4.62 (m, 1H), 1.58 (br s, 2H), 1.33 (d, J=6.43, 3H).

Workup

  1. extractionThen, the reaction was extracted with ethyl acetate-sodium hydroxide (1N) and brine
  2. customThe organic layer was collected
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto produce a crude, which it

Sources & evidence

ORD record
ord-ef03ea76be6a44fdb9b826c729a11592
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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