Ammonium Hydroxide → HCID 59596826, compound

HRID 1092396Notes

Reaction equation

HRID 1092396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[O:11][CH2:12][C:13]([F:16])([F:15])[F:14].[NH4+].[OH-]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][C:3]=1[O:11][CH2:12][C:13]([F:14])([F:16])[F:15]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59596840HCID 59596840, compound

Product 1

HCID 59596826HCID 59596826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

800 mg (10 mmol) of borane-methyl sulfide complex were added to a solution of 1.23 g (5.27 mmol) of [4-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-acetonitrile in 50 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 4 hours. Solvent was removed and then water was added. A first extraction with diethyl ether allowed to partially purify the crude reaction mixture. The resulting aqueous layer was then basified with NH4OH, and the product was extracted with dichloromethane. After removal of the solvent 1 g (80% yield) of the title compound was isolated as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customSolvent was removed
  3. additionwater was added
  4. extractionA first extraction with diethyl ether
  5. customto partially purify the crude
  6. customreaction mixture
  7. extractionthe product was extracted with dichloromethane

Sources & evidence

ORD record
ord-8e709c1c4d5d45bb89cf2c6f814db88d
Source dataset
uspto-grants-2012_03
Patent number
US08129427B2

Reaction notes

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