Water → HCID 22254478, compound

HRID 967081Notes

Reaction equation

HRID 967081 reaction equation
[O:1]([CH2:8][CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C.O>ClCCl>[N+:22]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[NH:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 156512-PhenoxyethanamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 22254478HCID 22254478, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 2-phenoxyethylamine (17.6 ml, 0.13 mol) was added dropwise to a chilled (ice bath) solution of 4-chloro-3-nitroquinoline (21.5 g, 0.1 mol), triethylamine (21.5 ml, 0.16 mol) in dichloromethane (500 ml). The reaction was maintained at ambient temperature overnight. Water was added and the phases were separated. The organic phase was dried (MgSO4), filtered, and the bulk of the solvent was removed under vacuum. Hexane was added and the solution was chilled in a refrigerator. The resulting precipitate was recovered by vacuum filtration to provide 19.1 g of 3-nitro-N-(2-phenoxyethyl)quinolin-4-amine as a yellow solid.

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe bulk of the solvent was removed under vacuum
  5. additionHexane was added
  6. temperaturethe solution was chilled in a refrigerator
  7. filtrationThe resulting precipitate was recovered by vacuum filtration

Sources & evidence

ORD record
ord-d9f3d7718a9c41a79de90885869c8cfc
Source dataset
uspto-grants-2005_10
Patent number
US06953804B2

Reaction notes

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