Water → HCID 59401298, compound

HRID 2060850Notes

Reaction equation

HRID 2060850 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]#[N:20].O.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[C:14]2[CH2:19][NH2:20]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13491715HCID 13491715, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59401298HCID 59401298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of LiAlH4 (244 mg, 6.44 mmol) in THF (30 mL) at rt under nitrogen was added 5-methoxynaphthalene-1-carbonitrile (Preparation 11) (513 mg, 2.80 mmol). The reaction mixture was heated to 90° C. for 3 h, then cooled to rt. Water (0.25 mL) was added followed by 1M NaOH (0.25 mL) and water (0.5 mL). The mixture was filtered through Celite and the solvent removed in vacuo to give the title compound: RT=1.99 min; m/z (ES+)=188.0 [M+H]+.

Workup

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered through Celite
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8456a24dc58b4169a39c62c194ea9811
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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