Sodium Sulfate → 2-Phenoxy-6-(phenylamino)benzylamine

HRID 1826842Notes

Reaction equation

HRID 1826842 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[C:22](F)=[CH:21][CH:20]=[CH:19][C:18]=2F)[C:9]=1[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[CH2:10][NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 221362282-Phenoxy-6-(2,6-difluorophenylamino)benzonitrile

Product 1

HCID 221362242-Phenoxy-6-(phenylamino)benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 1b above, 2-phenoxy-6-(2,6-difluorophenylamino)benzonitrile, (0.34 g, 1.06 mmol) was dissolved in dry tetrahydrofuran (40 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.384 g, 10.1 mmol) was added, and the reaction mixture was heated to 65° C. for 0.5 hour. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate. The solvent was evaporated and the residue triturated with ethyl acetate, filtered and evaporated. Flash chromatography on silica gel eluted with 40% methylene chloride/hexane to which 3% methanol was added followed by Gilson hplc purification gave the title compound as a white amorphous solid. mp 113–116° C.

Workup

  1. temperaturethe reaction mixture was heated to 65° C. for 0.5 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customby quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue triturated with ethyl acetate
  6. filtrationfiltered
  7. customevaporated
  8. washFlash chromatography on silica gel eluted with 40% methylene chloride/hexane to which 3% methanol
  9. additionwas added
  10. customfollowed by Gilson hplc purification

Sources & evidence

ORD record
ord-cd7236fbf856435b8f7c9aad07d72afb
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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