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

HRID 854035Notes

Reaction equation

HRID 854035 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:14]([OH:16])=O)[C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.Cl.[CH3:18][NH:19][CH3:20].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C>C(#N)C.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:14]([N:19]([CH3:20])[CH3:18])=[O:16])[C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=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

To a solution of 1,2,3,4-tetrahydro-7-methoxy-2-oxo-3-quinolinecarboxylic acid (3.74 g), dimethylamine hydrochloride (3.44 g), 1-hydroxybenzotriazole (2.85 g), and triethylamine (8.5 g) in acetonitrile (400 ml) was added WSC (6.5 g). The reaction mixture was stirred at room temperature for 24 hr and concentrated. The residue was diluted with ethyl acetate and the organic layer was washed with 1 N aqueous hydrochloric acid, 10% aqueous potassium carbonate, and saturated aqueous sodium chloride, dried, and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to obtain the titled compound (1.63 g).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethyl acetate
  3. washthe organic layer was washed with 1 N aqueous hydrochloric acid, 10% aqueous potassium carbonate, and saturated aqueous sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d431fa6599a547a981b0f99224e0fc42
Source dataset
uspto-grants-2007_08
Patent number
US07256204B2

Reaction notes

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