HCID 12017675, compound → HCID 12017676, compound

HRID 1006538Notes

Reaction equation

HRID 1006538 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[C:11]#[C:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)([O-])=O>C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[C:11]#[C:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 12017675HCID 12017675, compound

Product 1

HCID 12017676HCID 12017676, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 4-[2-(2-nitro-5-chlorophenyl)ethynyl]benzoate (180 mg; prepared in Reference Example 15.) in acetic acid (3.6 ml), reduced iron powder (160 mg) was added. The mixture was refluxed for 30 minutes and filtered. The filtrate was concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) to give the title compound (144 mg) having the following physical data.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. customThe residue was purified on silica gel column chromatography (hexane-AcOEt)

Sources & evidence

ORD record
ord-984461d43616452d9674f9b541097944
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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