4-Nitrophenol → HCID 18979049, compound

HRID 2393096Notes

Reaction equation

HRID 2393096 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:24])[C:9]1[CH:18]=[CH:17][C:16]2[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[C:12]([O:22][CH3:23])[C:11]=2[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[N+:37]([C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1)([O-:39])=[O:38]>ClCCl>[C:1]([O:5][C:6]([N:8]([CH3:24])[C:9]1[CH:18]=[CH:17][C:16]2[C:15]([C:19]([O:21][C:43]3[CH:44]=[CH:45][C:40]([N+:37]([O-:39])=[O:38])=[CH:41][CH:42]=3)=[O:20])=[CH:14][CH:13]=[C:12]([O:22][CH3:23])[C:11]=2[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18979078HCID 18979078, compound

Product 1

HCID 18979049HCID 18979049, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(t-Butyloxycarbonyl)(methyl)amino]-8-methoxyquinoline-5-carboxylic acid (0.311 g), ethyldimethylaminopropylcarbodiimide hydrochloride (0.269 g), 4-nitrophenol (0.195 g), N,N-dimethylaminopyridine (20 mg) and dichloromethane (20 ml) were combined and then stirred at room temperature for 17 h. The reaction mixture was evaporated in vacuo onto silica and purified by flash chromatography to give the title compound (0.384 g) as a pale yellow solid.

Workup

  1. customThe reaction mixture was evaporated in vacuo onto silica
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5b75149d38864c6c917dd6b2a6f26ed5
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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