Citric Acid → 1,2,3,4-Tetrahydro-N,N-dimethyl-2-oxo-3-quinolinecarboxamide

HRID 2269718Notes

Reaction equation

HRID 2269718 reaction equation
[O:1]=[C:2]1[CH:11]([C:12]([OH:14])=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.Cl.[CH3:16][NH:17][CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C.C(N(CC)CC)C>[CH3:16][N:17]([CH3:18])[C:12]([CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1])=[O:14]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 133204612-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid

Product 1

HCID 183331521,2,3,4-Tetrahydro-N,N-dimethyl-2-oxo-3-quinolinecarboxamideYield 97.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

2-Oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid (8.56 g), dimethylamine hydrochloride (4.60 g), HOBt (7.18 g), WSC (11.1 g) and triethylamine (20 ml) were added to acetonitrile (400ml). The reaction mixture was stirred at room temperature for 43 hours. 10% aqueous citric acid solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were washed with IPE to give the entitled compound (9.486 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated
  5. customThe obtained crude crystals
  6. washwere washed with IPE

Sources & evidence

ORD record
ord-931e97804f324909bd7b807be990e58f
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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