Hydrochloric Acid → HCID 59385318, compound

HRID 2356792Notes

Reaction equation

HRID 2356792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].Cl>C(O)C.[Fe]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385219Methyl 3-chloro-4'-nitrobiphenyl-4-carboxylate

Product 1

HCID 59385318HCID 59385318, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.99 g, 17.7 mmol) was added to a solution of methyl 3-chloro-4′-nitrobiphenyl-4-carboxylate (0.64 g, 1.8 mmol) in ethanol (15 mL). Concentrated HCl (0.88 mL, 1.8 mmol) was added, and the mixture was heated at reflux for 3 h. Upon cooling to rt, the mixture was filtered through a pad of Celite®, and the filtrate was concentrated in vacuo. The material was purified by column chromatography (33% EtOAc in hexanes), yielding 0.453 g (98%) of the title compound. LC/MS m/z 262.4 (Mob; retention time 2.39 min. 1H NMR (400 MHz, CD2Cl2) δ 3.99 (s, 3H), 6.78 (d, 2H), 7.41-7.46 (m, 3H), 7.62 (s, 1H), 7.88 (d, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationthe mixture was filtered through a pad of Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe material was purified by column chromatography (33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9af4ed57e262403f966ad74f965116f6
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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