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Water → (7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine

HRID 2383100
Notes
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Reaction equation

HRID 2383100 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20](Cl)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:30]([CH2:37][CH2:38][NH2:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>ClCCl>[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:39][CH2:38][CH2:37][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 156512-PhenoxyethanamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67050949(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amineYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Triethylamine (8.93 mL, 64.1 mmol) was added to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (13.45 g, 42.7 mmol), prepared in Parts A-D of Example 1, in dichloromethane (250 mL). 2-Phenoxyethylamine (6.15 mL, 47.0 mmol) was added dropwise over a period of ten minutes, and the reaction mixture was stirred for three hours at ambient temperature. Distilled water (200 mL) was added to the solution, and the aqueous layer was washed with dichloromethane (2×200 mL). The combined organic solutions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a solid. The solid was washed with hexanes, isolated by filtration, and dried under reduced pressure to provide 17.14 g of (7-benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine as a yellow solid.

Workup

  1. washthe aqueous layer was washed with dichloromethane (2×200 mL)
  2. dry with materialThe combined organic solutions were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto provide a solid
  6. washThe solid was washed with hexanes
  7. customisolated by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9e03d78770e4ca0a6e26ff46d6d0293
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263594B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes