Hydrochloric Acid → HCID 59385207, compound

HRID 2356794Notes

Reaction equation

HRID 2356794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].Cl>C(O)C.[Fe]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385322HCID 59385322, compound

Product 1

HCID 59385207HCID 59385207, compoundYield 108.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.58 g, 10 mmol) was added to a solution of methyl 3-methoxy-4′-nitrobiphenyl-4-carboxylate (0.38 g, 1.0 mmol) in ethanol (10 mL). Concentrated HCl (0.52 mL, 1.0 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 0.279 g (quantitative yield) of the title compound. LC/MS m/z 258.3 (MH+); retention time 1.65 min. 1H NMR (400 MHz, CD2Cl2) 3.81 (s, 3H), 3.99 (s, 3H), 6.78 (d, 2H), 7.15-7.19 (m, 2H), 7.45 (d, 2H), 7.80 (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-fe00b4e5065c4780bf89f4b097b8d1cc
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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