Benzofuran-4-carbonitrile → (1-Benzofuran-4-yl)methanamine

HRID 2041228Notes

Reaction equation

HRID 2041228 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10]#[N:11])=[C:4]2[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:11][CH2:10][C:9]1[C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 13307980Benzofuran-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 55291080(1-Benzofuran-4-yl)methanamineYield 138.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Dissolve benzofuran-4-carbonitrile (0.3 g, 1.96 mmol) in anhydrous THF (5 mL) and add slowly to 1M lithium aluminum hydride in THF (3.91 mL, 3.91 mmol) at ambient temperature. Heat the reaction mixture at 50° C. for 5 h and cool to ambient temperature. Quench the reaction mixture with water until a granular precipitate starts to form and filter through a pad of Celite®. Evaporate the solvent and purify by SCX chromatography to obtain the title compound as a brown oil (0.4 g, 79%). GC-MS m/z: 147 (M+).

Workup

  1. temperaturecool to ambient temperature
  2. customQuench the reaction mixture with water until a granular precipitate
  3. customto form
  4. filtrationfilter through a pad of Celite®
  5. customEvaporate the solvent
  6. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-b06aee626ec2457dad9d3d8becd4d63e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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