2-(Ethoxymethylene)propanedinitrile → 5-Cyano-1-(indol-5-yl)benzimidazole

HRID 2294158Notes

Reaction equation

HRID 2294158 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)=[C:5]([NH2:19])[CH:4]=1)#[N:2].[CH2:20](OC=C(C#N)C#N)C>C(O)CC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]2[N:9]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[CH:13]4)[CH:20]=[N:19][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 21474193HCID 21474193, compound

Product 1

HCID 214741665-Cyano-1-(indol-5-yl)benzimidazoleYield 94%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

5-(4-Cyano-2-nitrophenylamino)-1H-indole (0.56 g, 2.0 mmoles) was reduced by catalytic hydrogenation, to form 5-(4-cyano-2-aminophenylamino)-1H-indole (0.50 g, 2.0 mmole). The 5-(4-cyano-2-aminophenylamino)-1H-indole was cyclized using ethoxymethylenemalononitrile (0.49 g, 2.0 mmoles) in propanol, and the cyclization reaction was heated for 24 hours. Column chromatography using ethyl acetate/hexanes [1:1] afforded the title compound (94%) as a yellow solid. Mp, 263.0°-264.0° C.; 13C NMR (DMSO-d6) δ147.2, 143.5, 137.5, 135.8, 128.5, 128.1, 127.3, 127.0, 125.3, 120.2, 118.2, 116.7, 113.1, 112.6, 104.8, 102.2; HRMS calculated for C16H10N4 258.0904, found 258.0904. Analytical calculated for C16H10N4 : C, 74.40; H, 3.90; N, 21.69. Found: C, 74.20; H, 3.92; N, 21.69.

Workup

  1. customthe cyclization reaction
  2. temperaturewas heated for 24 hours

Sources & evidence

ORD record
ord-bab133111b90424c882efac5c83e2654
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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