8-Hydroxyquinoline → HCID 44553783, compound

HRID 714395Notes

Reaction equation

HRID 714395 reaction equation
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+].[CH2:35]([O:42][C:43]1[CH:48]=[CH:47][NH:46][C:45](=[O:49])[CH:44]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:46]2[CH:47]=[CH:48][C:43]([O:42][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:44][C:45]2=[O:49])[CH:11]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 15115857N-benzyl-2-chloropyridine-4-carboxamide

Product 1

HCID 44553783HCID 44553783, compoundYield 53.3%

Conditions

Temperature
110 °C

Procedure

A mixture of N-benzyl-2-chloroisonicotinamide (1.00 g, 4.06 mmol), copper iodide(I) (0.12 g, 0.61 mmol), 8-hydroxyquinoline (0.09 g, 0.61 mmol), potassium carbonate (0.84 g, 6.09 mmol), 4-(benzyloxy)pyridin-2(1H)-one (0.82 g, 4.06 mmol) in N,N-dimethylormamide (20 mL) was heated to 110° C. for 16 hours under nitrogen atmosphere and concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with water (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with 60-75% ethyl acetate in petroleum ether to give 4-benzyloxy-2-oxo-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as colorless solid (0.89 g, 53%): mp 158-161° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.60 (d, J=5.0 Hz, 1H), 8.19 (s, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.74 (d, J=5.0 Hz, 1H), 7.42-7.26 (m, 11H), 6.16-6.13 (m, 1H) 5.95 (d, J=2.3 Hz, 1H), 5.02 (s, 2H), 4.58 (d, J=5.6 Hz, 2H); MS (ES+) m/z 412.2 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with water (100 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified by column chromatography
  8. washeluting with 60-75% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0e606adc0fa745d39acc88cdfff02a68
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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