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

HRID 1967095Notes

Reaction equation

HRID 1967095 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 (0.90 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-1bb7ff6ba9bc429d84122ee97f1fa59b
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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