Water → HCID 86616895, compound

HRID 606117Notes

Reaction equation

HRID 606117 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:34]=[C:33]([CH2:35][CH2:36][NH2:37])[O:32][N:31]=2)=[CH:26][CH:25]=1.O>CN1CCCC1=O>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:37][CH2:36][CH2:35][C:33]2[O:32][N:31]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[CH:34]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinolineHCID 67041295HCID 67041295, compound

Product 1

HCID 86616895HCID 86616895, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
6 °C

Procedure

Under a nitrogen atmosphere, triethylamine (14.9 mL, 107 mmoL) was added to a solution of 2,4-dichloro-3-nitroquinoline (17.29 g, 71.15 mol) in anhydrous 1-methyl-2-pyrrolidinone (NMP) (100 mL). The mixture was stirred until it was homogeneous and then was cooled to 6° C. 2-[3-(4-Fluorophenyl)isoxazol-5-yl]ethylamine (14.9 mL, 107 mmol) was added dropwise over a period of 30 minutes; the temperature did not rise above 10° C. during the addition. After the reaction was stirred for 1.75 hours, deionized water (100 mL) was added. A precipitate formed, and the mixture was stirred for 30 minutes. The precipitate was isolated by filtration, and washed with deionized water until the filtrate was pH 8. The filter cake was then washed sequentially with toluene (100 mL) and a small amount of diethyl ether and dried for 18 hours to provide 27.84 g of 2-chloro-N-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-3-nitroquinolin-4-amine as a bright yellow solid.

Workup

  1. additionthe temperature did not rise above 10° C. during the addition
  2. stirringAfter the reaction was stirred for 1.75 hours
  3. customA precipitate formed
  4. stirringthe mixture was stirred for 30 minutes
  5. customThe precipitate was isolated by filtration
  6. washwashed with deionized water until the filtrate
  7. washThe filter cake was then washed sequentially with toluene (100 mL)
  8. dry with materiala small amount of diethyl ether and dried for 18 hours

Sources & evidence

ORD record
ord-19bae4a0b991422eb07db88670082d82
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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