Methyl iodide → 2-(5-nitro-1H-indol-3-yl)acetonitrile

HRID 1666840Notes

Reaction equation

HRID 1666840 reaction equation
C[N:2](C)[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[NH:7][CH:6]=1.IC.[C-]#N.[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[N+:14]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:4][C:3]#[N:2])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 9499653-(2-DIMETHYLAMINOETHYL)-5-NITROINDOLE

Product 1

HCID 2477542-(5-nitro-1H-indol-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve the N,N-dimethyl-5-nitrotryptamine obtained above in 200 mL dry DMSO, treat with iodomethane (7.7 mL, 17.5 g, 124 mmol), and stir for 1 hour at ambient temperature. Add KCN (40 g, 621 mmol) and 18-crown-6 (0.5 g). Warm the reaction to 110° C. for 45 minutes, cool, poured onto ice then saturate with NaCl. Extract the quenched reaction mixture with EtOAc, combine the extracts, and wash 3 times with brine. Dry over MgSO4 and concentrate under vacuum chromatograph on silica gel eluting with 1% MeOH in CHCl3 to give (5-nitro-1H-indol-3-yl)acetonitrile as a solid: FDMS 201 (M+); Analysis for C10H7N3O2: calcd: C, 59.70; H, 3.51; N, 20.89. found: C, 59.32; H, 3.52; N, 20.56.

Workup

  1. temperatureWarm
  2. customthe reaction to 110° C. for 45 minutes
  3. temperaturecool
  4. additionpoured onto ice
  5. concentrationthen saturate with NaCl
  6. extractionExtract
  7. customthe quenched reaction mixture with EtOAc
  8. washwash 3 times with brine
  9. dry with materialDry over MgSO4
  10. concentrationconcentrate under vacuum chromatograph on silica gel eluting with 1% MeOH in CHCl3

Sources & evidence

ORD record
ord-163df98c16a44213a1f9615cac85bdbe
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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