Aluminium lithium hydride → N-methyl-1,3-dihydro-2-benzofuran-5-amine

HRID 63644Notes

Reaction equation

HRID 63644 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][CH:11]=O)=[CH:9][C:4]=2[CH2:3][O:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O.CCOC(C)=O>[CH3:11][NH:10][C:8]1[CH:7]=[CH:6][C:5]2[CH2:1][O:2][CH2:3][C:4]=2[CH:9]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118597990HCID 118597990, compound

Product 1

HCID 23544376N-methyl-1,3-dihydro-2-benzofuran-5-amineYield 98.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(1,3-dihydro-2-benzofuran-5-yl)formamide (250 mg, 1.5 mmol) in THF (20 mL) was added LAH (1.9 mL, 2.4 M in THF, 4.6 mmol) at 0° C. The reaction was stirred at r.t. for 2 h. The solution was diluted with water (0.5 mL) and EtOAc (30 mL), dried (Na2SO4), and concentrated to give 220 mg (96%) of the title compound as a yellow oil. [M+H] Calc'd for C9H11NO, 150. Found, 150.

Workup

  1. dry with materialdried (Na2SO4)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a656235040a8474db99851f83a60a9df
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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