Malononitrile → HCID 69039427, compound

HRID 1826977Notes

Reaction equation

HRID 1826977 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[C:21](#[N:25])[CH2:22][C:23]#[N:24].N1CCCCC1>C(O)C>[NH2:25][C:21]1[O:1][CH:2]2[C:3]3[C:7](=[CH:8][CH:9]=[C:10]2[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH3:11])[CH:14]=2)[C:22]=1[C:23]#[N:24])[N:6]=[CH:5][CH:4]=3

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 115693-MethoxybenzaldehydeHCID 754211H-indol-4-ol

Product 1

HCID 69039427HCID 69039427, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxyindole (500 mg, 3.76 mmol), 3-methoxybenzaldehyde (511 mg, 3.76 mmol) and malononitrile (250 mg, 3.76 mmol) in ethanol (10 mL) was added piperidine (0.18 mL, 1.62 mmol). The solution was stirred at room temperature overnight and the solvent was removed in vacuo. The crude material was purified by flash column chromatography (3:1 hexane:ethyl acetate) to yield 300 mg (25%) of title compound as white solids. 1H NMR (CDCl3): 8.26 (brs, 1H), 7.26–7.18 (m, 2H), 7.09–7.06 (m, 1H), 6.84–6.74 (m, 4H), 6.65–6.63 (m, 1H), 4.80 (s, 1H), 4.65 (brs, 2H), 3.76 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude material was purified by flash column chromatography (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2269224c5bce435ea18d4675e618376e
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

Loading…