HCID 12017675, compound → HCID 12017676, compound

HRID 1279603Notes

Reaction equation

HRID 1279603 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-7ec8270ba0a94be3af984bb7351e1776
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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