Pyridine → HCID 59168391, compound

HRID 1443918Notes

Reaction equation

HRID 1443918 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12]([CH2:16][C:17](Cl)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1>ClCCl>[CH3:13][C:12]([CH3:15])([CH3:14])[CH2:16][C:17]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 113736-AminoquinolineHCID 815143,3-Dimethylbutanoyl chloride

Product 1

HCID 59168391HCID 59168391, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 1, Step 3, 6-nitroquinoline (2.5 g) and 5% palladium on carbon (0.10 g) in ethanol (40 mL) was hydrogenated to give 6-aminoquinoline (2.2 g). A mixture of 6-aminoquinoline (2.2 g, 15 mmol), t-butylacetyl chloride (2.2 mL, 16 mmol), and pyridine (2.5 mL, 31 mmol) in dichloromethane (40 mL) was then stirred at ambient temperature for 4 h and then extracted with 1 N HCl. The acidic layer was separated and treated with 50% NaOH until basic. The basic phase was extracted with dichloromethane. The combined extracts were dried (MgSO4) and concentrated. The crude material was triturated with hexane and the solid was collected by filtration to provide 3,3-dimethyl-N-quinolin-6-ylbutanamide (3.0 g). MS (ES) m/z 241.1.

Workup

  1. extractionextracted with 1 N HCl
  2. customThe acidic layer was separated
  3. additiontreated with 50% NaOH until basic
  4. extractionThe basic phase was extracted with dichloromethane
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was triturated with hexane
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-62337381918341f09ef95b873faf6282
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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