1-Methoxy-2-propanol → 3-Methyl-2-(4-quinolylamino)butanamide

HRID 333051Notes

Reaction equation

HRID 333051 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C@H:13]([C:17]([NH2:19])=[O:18])[CH:14]([CH3:16])[CH3:15].C(NC(C)C)(C)C.COCC(O)C>>[CH3:15][CH:14]([CH3:16])[CH:13]([NH:12][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:17]([NH2:19])=[O:18]

Participants

5

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 7912DiisopropylamineHCID 691404-ChloroquinolineHCID 445637Valinamide

Product 1

HCID 668354133-Methyl-2-(4-quinolylamino)butanamideYield 15.6%

Procedure

4-Chloroquinoline (0.82 g, 5 mmol), valinamide (0.64 g, 5.5 mmol) and diisopropylamine (1.9 ml, 11 mmol) were mixed with 1-methoxy-2-propanol (8 ml) and heated with stirring at reflux for 48 hours. The solvent was removed under reduced pressure, the residue was partitioned between water and ethyl acetate, the phases were separated, the aqueous phase was washed 3 times with ethyl acetate and basified with 50% NaOH. A precipitate formed that was filtered off and dried in air to give 0.2 g of a solid (0.78 mmol, 14%). MS (APCI) M/z=243.6 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. customthe phases were separated
  6. washthe aqueous phase was washed 3 times with ethyl acetate
  7. customA precipitate formed
  8. filtrationthat was filtered off
  9. customdried in air

Sources & evidence

ORD record
ord-618bec5cfa184f7ca67955c9ece47d02
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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