Hydrochloric Acid → HCID 12425844, compound

HRID 1912895Notes

Reaction equation

HRID 1912895 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[BH4-].[Na+].Cl>CCO.O>[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][CH:2]([C:1]#[N:5])[C:3]#[N:4])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 680234-FluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12425844HCID 12425844, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of malononitrile (3.15 mL, 50.0 mmol) in 50 mL of 95% EtOH, 4-fluorobenzaldehyde (5.28 mL, 50 mmol) was added and the mixture was stirred at room temperature overnight. The white solid precipitated out and this suspension was diluted with 25 mL of EtOH then treated with sodium borohydride (0.946 g, 25.00 mmol) in one portion. This mixture was stirred at ambient temperature for 2 hours until reaction was complete. Water and 1N HCl solution was added carefully to quench sodium borohydride. The precipitate was then filtered, washed with copious amount of water, air-dried to give 5.92 g of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.43 (m, 2H) 7.06-7.17 (m, 2H) 3.90 (t, J=6.78 Hz, 1H) 3.27 (d, J=6.72 Hz, 2H). MS (ESI) m/z 173.1 (M−H)−.

Workup

  1. customThe white solid precipitated out
  2. additionthis suspension was diluted with 25 mL of EtOH
  3. stirringThis mixture was stirred at ambient temperature for 2 hours until reaction
  4. customto quench sodium borohydride
  5. filtrationThe precipitate was then filtered
  6. washwashed with copious amount of water
  7. customair-dried

Sources & evidence

ORD record
ord-9b190d1b6101426a9e9127e217fe6458
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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