Ammonium Hydroxide → HCID 59596826, compound

HRID 1261458Notes

Reaction equation

HRID 1261458 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-6605818686154ecf8c0bb1ec3da95d30
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

Loading…