Ethyl Acetate → HCID 21474183, compound

HRID 2294159Notes

Reaction equation

HRID 2294159 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)=[C:4]([NH2:18])[CH:3]=1.[CH2:19](OC=C(C#N)C#N)C.C(OCC)(=O)C>C(O)CC.C(Cl)Cl>[NH:14]1[C:15]2[C:11](=[CH:10][C:9]([N:8]3[C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=4[N:18]=[CH:19]3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 671522-(Ethoxymethylene)propanedinitrileHCID 21474165HCID 21474165, compound

Product 1

HCID 21474183HCID 21474183, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(4-Methyl-2-nitrophenylamino)-1H-indole (0.47 g, 2.0 mmoles) was reduced by catalytic hydrogenation to form 5-(4-methyl-2-aminophenylamino)-1H-indole (0.41 g, 2.0 mmoles). The 5-(4-methyl-2-aminophenylamino)-1H-indole was cyclized with ethoxymethylenemalononitrile (0.49 g, 2.0 mmole) in propanol, while being heated for 14 hours. Column chromatography using 10% ethyl acetate in methylene chloride afforded the title compound (81%) as a yellow solid. Mp, 215.0°-216.0° C.; Rf =0.3 in 10% ethyl acetate in methylene chloride; 1H NMR (DMSO-d6) δ11.43 (br s, NH), 8.42 (s, 1H), 7.76 (d, J=1.4 Hz, 1H), 7.61 (d, J=8.4 Hz, 1H), 7.56 (d, J=0.5 Hz, 1H), 7.52 (t, J=2.6 Hz, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.30 (dd, J=8.5 and 1.7 Hz, 1H), 7.12 (br d, J=8.3 Hz, 1H), 6.56 (dd, J=2.7 and 0.9 Hz, 1H), 2.44 (s, 3H); 13C NMR (DMSO-d6) δ156.5, 144.3, 143.8, 137.2, 134.0, 130.0, 129.1, 128.0, 126.4, 119.7, 119.0, 117.3, 113.4, 111.7, 103.0, 21.6; FAB LRMS (m/z, relative intensity) 249 (23), 248 ([MH]+, 100); HRMS calculated for C16H13N3 247.1107, found 247.1092.

Workup

  1. temperaturewhile being heated for 14 hours

Sources & evidence

ORD record
ord-b30884e277ce4fc4ab15364acec0c75c
Source dataset
uspto-grants-1997_11
Patent number
US05688809

Reaction notes

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