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

HRID 1845363Notes

Reaction equation

HRID 1845363 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-2f37e5007c294e0fbb545dfb82c8e509
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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