Acrylonitrile → HCID 16072743, compound

HRID 1394886Notes

Reaction equation

HRID 1394886 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH:5]1([C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH:30]=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>>[C:1]([C:2]1[CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:12]2=[C:11]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[C:19]3[CH:18]=[CH:17][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=3[N:13]2[CH:3]=1)#[N:4]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 58765266HCID 58765266, compound

Product 1

HCID 16072743HCID 16072743, compound

Conditions

Temperature
100 °C

Procedure

Acrylonitrile (2 mL of 1.52 M in 1,4-dioxane, 3.04 mmol) was added to methyl 3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate (200 mg, 0.55 mmol) in a microwave vial. The vial was sealed and Triton® B (50 μL, 0.11 μmol) was added via syringe. The vial was heated in a microwave apparatus for 1 hr at 100° C. The solution was concentrated and the residue dissolved in methylene chloride. The solution was applied to a silica gel thick layer plate. The plated was eluted with hexanes-ethyl acetate (8:2). The product containing band was extracted with methylene chloride-methanol (3×). The combined extracts were concentrated and the residue recrystallized from methanol to afford the titled compound as a tan solid. MS m/z 397 (MH); 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.16-2.25 (m, 10 H) 2.90-3.10 (m, 1 H) 3.20-3.34 (m, 1 H) 3.60-3.75 (m, 1H) 3.95 (s, 3 H) 7.28-7.49 (m, 4 H) 7.76 (s, 1 H) 7.86-7.97 (m, 2 H) 8.13 (s, 1 H).

Workup

  1. customThe vial was sealed
  2. additionTriton® B (50 μL, 0.11 μmol) was added via syringe
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue dissolved in methylene chloride
  5. washThe plated was eluted with hexanes-ethyl acetate (8:2)
  6. additionThe product containing band
  7. extractionwas extracted with methylene chloride-methanol (3×)
  8. concentrationThe combined extracts were concentrated
  9. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-9e1ff0ff8cba4cb6a26c728bc239d4b4
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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