Water → 6-((5-Formylquinolin-8-yl)oxy)nicotinonitrile

HRID 2060875Notes

Reaction equation

HRID 2060875 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].O>S1(CCCC1)(=O)=O>[CH:12]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][N:16]=2)=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2753638-Hydroxyquinoline-5-carbaldehydeHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 594013406-((5-Formylquinolin-8-yl)oxy)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 8-hydroxyquinoline-5-carbaldehyde (692 mg, 4 mmol) in sulfolane (8 mL) was added 2-chloro-5-cyanopyridine (552 mg, 4 mmol) and K2CO3 (1.7 g, 12 mmol). The reaction was heated at 90° C. for 2 h in a microwave. The reaction was cooled to rt and poured into water (100 mL). The resulting solid was filtered, washed with water, ether and air dried to give the title compound: RT=3.02 min; m/z (ES+)=276.0 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationThe resulting solid was filtered
  3. washwashed with water, ether and air
  4. customdried

Sources & evidence

ORD record
ord-13cb8150562e4fca82b760fcbc563d26
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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