Sodium Hydroxide → 2-Amino-1-(2-fluorophenyl)ethan-1-ol

HRID 434375Notes

Reaction equation

HRID 434375 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.[I-].[Zn+2].[I-].O>[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]([OH:11])[CH2:5][NH2:6]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 67970o-FluorobenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydride

Product 1

HCID 150671762-Amino-1-(2-fluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Trimethylsilyl cyanide (8.5 g) was added to a stirred mixture of 2-fluorobenzaldehyde (10.6 g) and zinc iodide (500 mg) in dry ether (150 ml). The mixture was stirred at ambient temperature for 24 hours and was then added dropwise to a stirred suspension of lithium aluminium hydride (3.2 g) in dry ether (50 ml) under nitrogen. The mixture was refluxed for 2 hours, cooled and water (3.2 ml), 2 N sodium hydroxide solution (3.2 ml) and water (9.6 ml) slowly added. The precipitate was filtered off, the filtrate was dried (MgSO4) and evaporated to a yellow oil (13.0 g) which crystallised slowly on standing.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. dry with materialthe filtrate was dried (MgSO4)
  5. customevaporated to a yellow oil (13.0 g) which
  6. customcrystallised slowly

Sources & evidence

ORD record
ord-28e4cc7135714dd084b0361d22468638
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

Loading…