3-Pyridineacetonitrile → HCID 54292959, compound

HRID 726669Notes

Reaction equation

HRID 726669 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]#[N:21])[CH:14]=1.C[O-].[Na+]>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[C:19]([C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)[C:20]#[N:21])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 809233-PyridineacetonitrileHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 54292959HCID 54292959, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde (4.92 g; 0.03 mol) and 3-pyridylacetonitrile (3.54 g; 0.03 mol) in ethanol (100 mL) was added sodium methoxide (6.48 g, of 25% methanol solution, 0.03 mol). The mixture was allowed to stand at ambient temperature for 18 hours. The mixture was concentrated to half volume. The solid was collected by filtration and dried to give 7.0 g (88.4% yield) of the title compound as an off-white solid, m.p. 158°-159° C. Anal. Calcd. for C16H12N2O2 : C, 72.72; H, 4.58; N, 10.60. Found: C, 72.53; H, 4.48; N, 10.97. Mass spectrum (DEI; M+) m/z 264. 1 H-NMR (DMSO-d6 ; 400 MHz) δ 8.91 (d, 1H), 8.59 (d, 1H), 8.08 (d, 1H), 8.00 (s, 1H), 7.57 (d, 1H), 7.47-7.53 (m, 2H), 7.02 (d, 2H), and 4.31 ppm (m, 4H).

Workup

  1. concentrationThe mixture was concentrated to half volume
  2. filtrationThe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-aec13135fdd448a18b08248a2571dea7
Source dataset
uspto-grants-1998_01
Patent number
US05710164

Reaction notes

Loading…