Hydrochloric Acid → HCID 19779539, compound

HRID 2082090Notes

Reaction equation

HRID 2082090 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]3[CH2:16][C:15](=[N:17][OH:18])[CH2:14]3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.B.N1C=CC=CC=1.Cl.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]3[CH2:16][CH:15]([NH:17][OH:18])[CH2:14]3)[CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6331BoraneHCID 14798Sodium HydroxideHCID 19779533HCID 19779533, compound

Product 1

HCID 19779539HCID 19779539, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-(4-fluorophenoxy)phenyl)cyclobutanone oxime from above, in ethanol (50 mL) was added borane.pyridine (2.06 g, 22.2 mmol) and the resulting solution was stirred for 30 min. 6N aqueous HCl (5.05 mL, 30.3 mmol) was then added dropwise and the reaction was stirred for 30 min. It was then neutralized by the addition of 2N aqueous NaOH and the ethanol evaporated in vacuo. The resulting residue was further diluted with brine to a volume of approximately 50 mL and extracted with ethyl acetate (3×50 mL). The organics were combined, dried over MgSO4 and concentrated to afford 3-(3-(4-flurophenoxy)phenyl)-1-cyclobutylhydroxylamine which was used as is.

Workup

  1. customthe ethanol evaporated in vacuo
  2. additionThe resulting residue was further diluted with brine to a volume of approximately 50 mL
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-183a139551e2470b9d624e474cbff2d3
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

Loading…