Hydrochloric Acid → HCID 15747440, compound

HRID 510398Notes

Reaction equation

HRID 510398 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[C:6]1([CH:16]=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+].Cl>C(O)C.O>[C:6]1([CH2:16][CH:2]([C:1]#[N:5])[C:3]#[N:4])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 61951-NaphthaldehydeHCID 8010MalononitrileHCID 4311764Sodium borohydride

Product 1

HCID 15747440HCID 15747440, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of malononitrile (1.32 g, 20 mmol) in Ethanol (50 mL) and Water (2.50 mL) was added 1-naphthalenecarbaldehyde (3.12 g, 20 mmol). The reaction was stirred at rt for 7 days. The mixture was cooled to 0° C. in an ice bath. Sodium borohydride (0.204 g, 5.40 mmol) was introduced to the vigorously stirred mixture and the reduction was complete in about 10 min. To the reaction mixture was added water (20 mL). 1N HCl was added in to quench the excess hydride. More water was added in until precipitation was complete. Filtration gave (1-naphthalenylmethyl)propanedinitrile (3.3 g, 80%). To a solution of (1-naphthalenylmethyl)propanedinitrile (3.3 g, 16 mmol) in Ethanol (80 mL) was added hydrazine hydrate (0.785 mL, 16.00 mmol). The mixture was heated at reflux temperature for 8 h. The reaction mixture was concentrated. The crude material was purified on a silica column (MeOH/DCM: 0˜10%) to give the product (2.18 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 2H) 7.26 (d, J=7.07 Hz, 1H) 7.31-7.44 (m, 1H) 7.45-7.58 (m, 2H) 7.74 (d, J=8.08 Hz, 1H) 7.85-7.97 (m, 1H) 8.12-8.26 (m, 1H) 10.05 (bs, 1H). LC/MS: MS (ES+) m/e 239.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to 0° C. in an ice bath
  2. waitthe reduction was complete in about 10 min
  3. customto quench the excess hydride
  4. additionMore water was added in until precipitation
  5. filtrationFiltration

Sources & evidence

ORD record
ord-201a8ab8b38a48359b800a645954ebce
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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