4-Quinolinecarboxaldehyde → HCID 54080304, compound

HRID 726668Notes

Reaction equation

HRID 726668 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH: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+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[CH:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[C:20]#[N:21])[CH:14]=1

Participants

6

Reactant 4

HCID 780724-QuinolinecarboxaldehydeHCID 809233-PyridineacetonitrileHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 54080304HCID 54080304, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Quinolin-4-carboxaldehyde (4.71 g; 0.03 mol) and 3-pyridylacetonitrile (3.54 g; 0.03 mol) were dissolved in ethanol (100 mL). Sodium methoxide (2 mL of 25% methanol solution) was added. The reaction mixture was heated at reflux for a period of 2.5 hours. The mixture was cooled to ambient temperature. After 18 hours, the precipitated solid was collected, suspended in ethanol and saturated with hydrogen chloride gas. The mixture was cooled and the solid was collected by filtration. The solid was crystallized from methanol to give the title compound (5.8 g; 57% yield) as a dihydrochloride, three quarter hydrate, yellow solid, m.p. 250° C. (dec.). Anal. Calcd for C17H11N3 ·HCl·3/4 H2O; C, 59.40; H, 4.25; N, 12.23. Found: C, 59.75; H, 4.10; N, 11.93. Mass spectrum (EI; M+) m/z 257. 1 H-NMR (DMSO-d6 ; 400 MHz) δ 9.40 (s, 1H), 9.38 (d, 1H), 9.15 (s, 1H), 8.93 (d, 1H), 8.74 (d, 1H), 8.56 (d, 1H), 8.46 (d, 1H), 8.32 (d, 1H), 8.13 (t, 1H), 8.00 (q, 1H), 7.95 (t, 1H), and 7.70 ppm (br s, 4H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for a period of 2.5 hours
  3. customthe precipitated solid was collected
  4. temperatureThe mixture was cooled
  5. filtrationthe solid was collected by filtration
  6. customThe solid was crystallized from methanol

Sources & evidence

ORD record
ord-828ae498def84da0a029324b5375e729
Source dataset
uspto-grants-1998_01
Patent number
US05710164

Reaction notes

Loading…