Aluminium lithium hydride → 3-Methoxyaniline

HRID 1481669Notes

Reaction equation

HRID 1481669 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2C(C(=O)NC3C=CC=CC=3)=CN=C(S(C)(=O)=O)N=2)[CH:9]=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH2:7]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59174704HCID 59174704, compound

Product 1

HCID 108243-MethoxyanilineYield 180.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7 (0.4 g, 0.9 mmol) in THF (10 mL) was added LAH (1.8 mL, 1.8 mmol) at −78° C. The reaction mixture was allowed to stir at the same temperature for 30 mins after which it was quenched with Na2SO4 solution (2 mL) and extracted with ethyl acetate (10 mL). The ethyl acetate layer was separated and washed with water (2 mL), brine solution (2 mL) and dried over anhydrous Na2SO4. Filtration followed by concentration under reduced pressure offered a residue which was purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate 7/3) to get 8 (200 mg, 58%) as a yellow solid.

Workup

  1. customwas quenched with Na2SO4 solution (2 mL)
  2. extractionextracted with ethyl acetate (10 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (2 mL), brine solution (2 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration
  7. concentrationfollowed by concentration under reduced pressure
  8. customwas purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-ada7bd04cf0447968c72d1de2c06f990
Source dataset
uspto-grants-2016_08
Patent number
US09409921B2

Reaction notes

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