N-(2-Methylquinolin-8-yl)acetamide → HCID 9920694, compound

HRID 899672Notes

Reaction equation

HRID 899672 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt](=O)=O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([NH:12][C:13](=[O:15])[CH3:14])[C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 14000972N-(2-Methylquinolin-8-yl)acetamide

Product 1

HCID 9920694HCID 9920694, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Conditions

Temperature
60 °C

Procedure

To a 3-neck, 500 mL round bottom flask containing a stir bar was added 2-methyl-8-acetamidoquinoline (5.69 g, 28.4 mmol) and platinum(IV) oxide (322 mg, 5 mol %). The flask was equipped with two Teflon cannulae: one for purging of the reaction flask with nitrogen gas and introduction of hydrogen, and the other leading to a flask connected to a bubbler. Trifluoroacetic acid (100 mL) was added to the reaction flask under an atmosphere of nitrogen. The stirred reaction mixture was flushed with nitrogen gas and warmed to 60° C. Hydrogen gas was bubbled through the stirred reaction for 3 h. The progress of the reaction was monitored by GC and/or TLC. The reaction mixture was cooled to room temperature, purged with nitrogen gas and the catalyst was filtered through a pad of Celite and washed with CH2Cl2 (100 mL). The solvent was removed in vacuo and the residue was basified with saturated NaOH (pH>14). The mixture was then extracted with CHCl3 (3×250 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by flash chromatography using 10% MeOH in EtOAc to provide the product (3.83 g, 66%) as a white solid. 1H NMR δ 1.57-1.66 (m, 1H), 1.77-1.86 (m, 2H), 2.02 (s, 3H), 2.44 (s, 3H), 2.43-2.57 (m, 1H), 2.68-2.73 (m, 2H), 4.67-4.74 (m, 1H), 6.79 (br s, 1H), 6.92 (d, 1H, J=8 Hz), 7.24 (d, 1H, J=8 Hz); 13C NMR δ 21.6, 25.4, 25.8, 29.6, 31.0, 53.0, 123.4, 131.4, 139.2, 155.9, 157.2, 172.2; ES-MS m/z: 227 (M+Na+).

Workup

  1. additionTo a 3-neck, 500 mL round bottom flask containing a stir bar
  2. customone for purging of the reaction flask with nitrogen gas and introduction of hydrogen
  3. customthe other leading to a flask
  4. additionTrifluoroacetic acid (100 mL) was added to the reaction flask under an atmosphere of nitrogen
  5. customThe stirred reaction mixture
  6. customwas flushed with nitrogen gas
  7. customHydrogen gas was bubbled through the stirred reaction for 3 h
  8. temperatureThe reaction mixture was cooled to room temperature
  9. custompurged with nitrogen gas
  10. filtrationthe catalyst was filtered through a pad of Celite
  11. washwashed with CH2Cl2 (100 mL)
  12. customThe solvent was removed in vacuo
  13. extractionThe mixture was then extracted with CHCl3 (3×250 mL)
  14. dry with materialThe organic extracts were dried (MgSO4)
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-a33a3d2078d349d8b1862d6612b196c7
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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