Malononitrile → HCID 10448627, compound

HRID 490840Notes

Reaction equation

HRID 490840 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[OH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][N:20]2[CH3:25].N1CCCCC1>C(O)C>[NH2:13][C:12]1[O:15][C:16]2[C:24]([CH:5]([C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=3)[C:11]=1[C:10]#[N:14])=[CH:23][CH:22]=[C:21]1[N:20]([CH3:25])[CH:19]=[CH:18][C:17]=21

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 680093-FluorobenzaldehydeHCID 158257394-Hydroxy-1-methylindole

Product 1

HCID 10448627HCID 10448627, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-fluorobenzaldehyde (46 mg, 0.37 mmol) and malononitrile (25 mg, 0.37 mmol) in ethanol (1 mL) was added 4-hydroxy-1-methyl-indole (55 mg, 0.37 mmol) followed by piperidine (0.02 mL, 0.19 mmol, 0.5 eq.). Reaction mixture was stirred at room temperature overnight. The desired compound precipitated and was collected, washed with ethanol and dried, yielding 36 mg of a yellow solid. 1H NMR (CDCl3): 7.28-7.23 (m, 1H), 7.05-7.01 (m, 3H), 6.92-6.86 (m, 2H), 6.74 (d, J=8.4 Hz, 1H), 6.56 (d, J=3.1 Hz, 1H), 4.84 (s, 1H), 4.67 (s, 2H), 3.76 (s, 3H).

Workup

  1. customReaction mixture
  2. customThe desired compound precipitated
  3. customwas collected
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-2ef0a8c177d74bf8868558a0c221f92c
Source dataset
uspto-grants-2009_05
Patent number
US07528164B2

Reaction notes

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