Ethanol → HCID 9997363, compound

HRID 490814Notes

Reaction equation

HRID 490814 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])=[CH:2]1.[C:16](#N)CC#N.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=CC=2)[C:23](C=O)=[CH:22]1.[CH3:32][CH2:33][OH:34]>N1CCCCC1>[NH2:13][C:12]1[O:34][C:33]2[C:26]([CH:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[C:11]=1[C:14]#[N:15])=[CH:25][CH:24]=[C:29]1[N:21]([CH3:16])[CH:22]=[CH:23][C:32]=21

Participants

6

Reactant 4

HCID 702EthanolHCID 8010MalononitrileHCID 10256Indole-3-CarboxaldehydeHCID 269623[(1H-Indol-3-yl)methylidene]propanedinitrile

Product 1

HCID 9997363HCID 9997363, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

2-(Indol-3-ylmethylene)-malononitrile: A yellow suspension of malononitrile (0.114 g, 1.72 mmol), anhydrous EtOH (1.72 mL), indole-3-carboxaldehyde (0.250 g, 1.72 mmol), and piperidine (6.8 μL, 0.069 mmol) was heated to form a yellow solution. Within 5 min, a yellow precipitate was formed and the reaction mixture was cooled to room temperature over 15 min. The yellow precipitate was filtered and collected, yielding 0.250 g (75%) of the title compound as a yellow solid.

Workup

  1. temperaturewas heated
  2. customto form a yellow solution
  3. customa yellow precipitate was formed
  4. filtrationThe yellow precipitate was filtered
  5. customcollected

Sources & evidence

ORD record
ord-e2553fedb72d448792b3dc49d9e92aec
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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