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

HRID 2228724Notes

Reaction equation

HRID 2228724 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 aluminium 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-1007a9f6075a4783a39aad12b89597b0
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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