Water → Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

HRID 1788404

Reaction equation

HRID 1788404 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>C(#N)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Product 1

HCID 5298559Ethyl 4-(cyclohexylamino)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Compound 9 (22.96 g, 100 mmol), cyclohexylamine (15.31 g, 154 mmol) and TEA (13.57 g, 134 mmol) in 100 mL acetonitrile was refluxed overnight. The reaction mixture was poured into icy water and the precipitated crystals were collected by means of filtration, washed three times with water then was dried over phosphorous pentoxide in high vacuum to yield Compound 10.

Workup

  1. filtrationthe precipitated crystals were collected by means of filtration
  2. washwashed three times with water
  3. dry with materialthen was dried over phosphorous pentoxide in high vacuum

Sources & evidence

ORD record
ord-f5e0bd8ff69a4e21abafde0eae58e9a5
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Linked notes

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