Indole-5-carbonitrile → (1H-indol-5-yl)methanamine

HRID 567801Notes

Reaction equation

HRID 567801 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])(O)=O.[Na+]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 27513Indole-5-carbonitrileHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 54791(1H-indol-5-yl)methanamineYield 314%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 1H-indole-5-carbonitrile (4.0 g, 28.1 mmol) in THF (50 ml) at 0° C. was treated dropwise with lithium aluminum hydride in THF (1M, 98 ml, 98 mmol). The resultant mixture was stirred, warming to room temperature overnight. Sat. aq. NaHCO3 (60 ml) was added at 0° C. and resultant mixture was filtered through filter agent celite 521 and washed with THF. Evaporation of the solvent gave the crude product which was purified by chromatography (SiO2, gradient elution with 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3) to give the desired product (white powder, 12.9 g, 71%). 1H NMR (CD3OD) δ 4.10 (s, 2H), 6.50 (d, 1H), 7.15 (d, 1H), 7.30 (d, 1H), 7.40 (d, 1H), 7.60 (s, 1H). LRMS m/z=147.2 (M+1)+.

Workup

  1. filtrationresultant mixture was filtered
  2. filtrationthrough filter agent celite 521
  3. washwashed with THF
  4. customEvaporation of the solvent
  5. customgave the crude product which
  6. customwas purified by chromatography (SiO2, gradient elution with 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3)

Sources & evidence

ORD record
ord-89cd23090aa74a8ba08adfbb149b1cba
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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