HCID 10797539, compound → 2-Amino-1-(naphthalen-1-yl)ethan-1-ol

HRID 1960992Notes

Reaction equation

HRID 1960992 reaction equation
[OH:1][CH:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[NH2:4][CH2:3][CH:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)[OH:1]

Participants

4

Reactant 2

HCID 10797539HCID 10797539, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 167681362-Amino-1-(naphthalen-1-yl)ethan-1-olYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hydroxy(1-naphthalenyl)acetonitrile (1.67 g, 9.14 mol) in THF (90 mL) at 0° C. was added dropwise a solution of LAH-THF (1M, 11 mL, 11 mmol). After 2 hrs, the solution was quenched by sequential addition of H2O (0.42 mL), 6N NaOH (6M, 0.32 mL) and H2O (1.6 mL). The resulting precipitate was filtered and the filtrate was concentrated and used directly yielding the title compound (0.897 g, 4.8 mmol, 53%) as a clear oil: LCMS (ES) m/z 188 (M+H)+.

Workup

  1. customthe solution was quenched by sequential addition of H2O (0.42 mL), 6N NaOH (6M, 0.32 mL) and H2O (1.6 mL)
  2. filtrationThe resulting precipitate was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ba001278effe47ae9713a16629aa6fbb
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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