Sodium Carbonate → HCID 10360448, compound

HRID 1352509Notes

Reaction equation

HRID 1352509 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH:11]1([N:14]([C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C@@H:20]([CH3:28])[CH2:19]2)[C:15](=[O:17])[CH3:16])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[CH:11]1([N:14]([C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([C:2]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)=[O:9])[C@@H:20]([CH3:28])[CH2:19]2)[C:15](=[O:17])[CH3:16])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 69429229HCID 69429229, compound

Product 1

HCID 10360448HCID 10360448, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Nicotinoyl chloride hydrochloride (1.46 g) was added to a solution of Cis-N-cyclopropyl-N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-acetamide (0.4 g) in pyridine (20 ml). The mixture was heated at 50° C. for 3 hours. After cooling, an aqueous solution of sodium carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and then the solvent was removed under reduce pressure. The crude compound was crystallized in diethyl ether to give Cis-N-cyclopropyl-N-[2-methyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydroquinolin-4-yl]-acetamide (0.3 g, 52.6% yield).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed
  5. customThe crude compound was crystallized in diethyl ether

Sources & evidence

ORD record
ord-7f8fff2923cd470baae6faf3ef0a8eab
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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