2-Phenoxyethanamine → (3-Nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine

HRID 9401Notes

Reaction equation

HRID 9401 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[O:21]([CH2:28][CH2:29][NH2:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C>[N+:18]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:30][CH2:29][CH2:28][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:10][CH:9]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:7]=2)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 156512-PhenoxyethanamineHCID 219843354-Chloro-3-nitro-7-phenylquinoline

Product 1

HCID 21984122(3-Nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amineYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Chloro-3-nitro-7-phenylquinoline (6.0 g, 21 mmol) was treated with 2-phenoxyethylamine (3.18 g, 23.2 mmol) according to the method described in Part A of Examples 125–135. The crude solid was triturated with water (100 mL), isolated by filtration, sonicated with diethyl ether, isolated by filtration, and dried for two hours in a vacuum oven at 40° C. to provide 8.12 g of (3-nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine as a yellow solid.

Workup

  1. customThe crude solid was triturated with water (100 mL)
  2. customisolated by filtration
  3. customisolated by filtration
  4. customdried for two hours in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-f72f99ec1a3a4a8dbe5376dce345964e
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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