Water → HCID 22254478, compound

HRID 1611787Notes

Reaction equation

HRID 1611787 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 anitrogen 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-4ad3223418064b3c8c876960b034e4c3
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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