Dimethylamine, hydrochloride → 7-Methoxy-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide

HRID 2269726Notes

Reaction equation

HRID 2269726 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH:19]([C:25]([OH:27])=O)[C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1.Cl.CNC.C1C=CC2N(O)N=NC=2C=1>C(N(CC)CC)C.C(#N)C>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH:19]([C:25]([N:3]([CH3:4])[CH3:2])=[O:27])[C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 229986197-Methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid

Product 1

HCID 229986357-Methoxy-N,N-dimethyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamideYield 38.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

WSC (6.5 g) was added to an acetonitrile solution of 7-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid (3.74 g), dimethylamine hydrochloride (3.44 g), HOBt (2.85 g) and triethylamine (8.5 g). The reaction mixture was stirred at room temperature for 24 hours and concentrated. The residue was diluted with ethyl acetrate. The organic layer was washed with 1N aqueous hydrochloric acid solution, 10% aqueous potassium carbonate solution, and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (1.63 g).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethyl acetrate
  3. washThe organic layer was washed with 1N aqueous hydrochloric acid solution, 10% aqueous potassium carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, then dried
  5. concentrationconcentrated
  6. customThe obtained crude crystals
  7. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e11b771abfdd4a59ab5e738ee9b7baaa
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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