Ammonium Acetate → HCID 15458590, compound

HRID 2270087Notes

Reaction equation

HRID 2270087 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10](Cl)[C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])(=O)C.[NH4+].[H][H]>[Pd].C(O)(=O)C>[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 15458589HCID 15458589, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15458590HCID 15458590, compoundYield 127.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.23 g of 2,3-dimethyl-4-chloro-8-methoxy-quinoline, 1 g of ammonium acetate, 20 ml of acetic acid and 1.2 g of palladium-on-charcoal (5%) are introduced into a Parr flask. The mixture is subjected to a hydrogen pressure of 50 psi for 4 h. The reaction medium is filtered and neutralized with 75 ml of 1 N sodium hydroxide. This mixture is extracted with ethyl acetate (2×75 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. 1.32 g (yield: 77%) of 2,3-dimethyl-8-methoxyquinoline are obtained—m.p.: 138-139° C.

Workup

  1. filtrationThe reaction medium is filtered
  2. extractionThis mixture is extracted with ethyl acetate (2×75 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e02c0abe5a5348ac9a0ef1c191847613
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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