Water → HCID 15766689, compound

HRID 1707570Notes

Reaction equation

HRID 1707570 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH3:30])([CH3:29])[CH:23]=[CH:22]2.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1)[C:24]([CH3:30])([CH3:29])[CH:23]=[CH:22]2

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 15711966HCID 15711966, compound

Product 1

HCID 15766689HCID 15766689, compoundYield 16.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5.34 g of nicotinic acid chloride hydrochloride was suspended in 50 ml of methylene chloride and 7.56 g of triethylamine was added thereto. After the resulting suspension was stirred at room temperature for 30 minutes, 3.88 g of 6-chloro-2,2-dimethyl-1,2-dihydroquinoline dissolved in 20 ml of methylene chloride was added thereto. Further, 1.00 g of 4-dimethylaminopyridine was added thereto. After refluxing the resulting solution mixture for 7 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer separated from the aqueous layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was subjected to thin-layer chromatography (silica gel; ethyl acetate/hexane 1:1 (V/V)) to obtain 1.01 g of 6-chloro-2,2-dimethyl-1-nicotinoyl-1,2-dihydroquinoline (the present compound (1)).

Workup

  1. additionwas added
  2. temperatureAfter refluxing the resulting solution mixture for 7 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic layer separated from the aqueous layer
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue obtained

Sources & evidence

ORD record
ord-8e0c4ffc8f1d4c96b0c1b21292c5039c
Source dataset
uspto-grants-1994_10
Patent number
US05354729

Reaction notes

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