Acetic Acid → N-(1,2,3,4-tetrahydroquinolin-5-yl)acetamide

HRID 48218Notes

Reaction equation

HRID 48218 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-])=O.[C:14](O)(=[O:16])[CH3:15]>C(OC(=O)C)(=O)C.[Pd].O=[Pt]=O>[NH:9]1[C:10]2[C:5](=[C:4]([NH:1][C:14](=[O:16])[CH3:15])[CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 118295-Nitroquinoline

Product 1

HCID 10081242N-(1,2,3,4-tetrahydroquinolin-5-yl)acetamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 5-nitroquinoline (50 g, 0.29 mol) in 1 L acetic acid and 30 mL acetic anhydride was treated with 5% Pd/C (3 g) and shaken on a Parr apparatus under a H2 atmosphere (50.8 psi) for 10.4 hours. The reaction was then treated with PtO2 (1 g) and recharged with H2 (50.8 psi) and shaken an additional 2 hours. After removing the catalyst by filtration, the filtrate was evaporated and the residue was separated between methylene chloride and water. The aqueous layer was basified with 50% NaOH and washed with methylene chloride. The combined organic layer was dried over sodium sulfate, filtered, and evaporated. The resulting solid was crystallized from ethyl acetate (23 g, 42%).

Workup

  1. stirringshaken an additional 2 hours
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. customthe filtrate was evaporated
  5. customthe residue was separated between methylene chloride and water
  6. washwashed with methylene chloride
  7. dry with materialThe combined organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting solid was crystallized from ethyl acetate (23 g, 42%)

Sources & evidence

ORD record
ord-f5fed8251d324bddab87595d8cbb424c
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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