Ethyl Acetate → HCID 58525582, compound

HRID 1894976Notes

Reaction equation

HRID 1894976 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[OH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][C:16]([C:22]([OH:24])=[O:23])=[CH:15]2.C(=O)([O-])[O-].[Cs+].[Cs+].CC(=O)OCC>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][C:16]([C:22]([OH:24])=[O:23])=[CH:15]3)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 7351522-Chloro-4-nitropyridineHCID 589024556-Hydroxyquinoline-3-carboxylic acid

Product 1

HCID 58525582HCID 58525582, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-4-nitropyridine (0.228 g, 1.44 mmol), 6-hydroxyquinoline-3-carboxylic acid (Int-15, 0.3 g, 1.58 mmol), and cesium carbonate (1.41 g, 4.32 mol) in N,N-dimethylformamide (3 mL) was heated at 150° C. for 2 h in a microwave reactor. The reaction was cooled to room temperature and filtered to remove solids. The filtrate was acidified with hydrochloric acid (1 M in water) until pH 1.5. The product precipitated cleanly and was isolated by suction filtration. LC-MS: (FA) EA+ 301; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.31 (d, J=2.1 Hz, 1H), 8.98 (d, J=2.0 Hz, 1 H), 8.34 (d, J=5.7 Hz, 1H), 8.21 (d, J=9.1 Hz, 1H), 8.06 (d, J=2.7 Hz, 1H), 7.79 (dd, J=9.1, 2.8 Hz, 1H), 7.20 (d, J=2.2 Hz, 1H), 7.09 (dd, J=5.7, 2.3 Hz, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customto remove solids
  4. customThe product precipitated cleanly
  5. customwas isolated by suction filtration

Sources & evidence

ORD record
ord-f3e9017e2d7849e38f9d215350bdd2d8
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

Loading…