Hydrochloric Acid → Methyl 4'-amino-3-methylbiphenyl-4-carboxylate

HRID 2356790Notes

Reaction equation

HRID 2356790 reaction equation
[CH3:1][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]([CH3:1])[CH:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385226Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

Product 1

HCID 59385243Methyl 4'-amino-3-methylbiphenyl-4-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (1.04 g, 18.6 mmol) was added to a solution of methyl 3-methyl-4′-nitrobiphenyl-4-carboxylate (0.63 g, 1.9 mmol) in ethanol (20 mL). Concentrated HCl (0.93 mL, 1.9 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 0.338 g (75%) of the title compound. LC/MS m/z 242.3 (MH+); retention time 2.27 min. 1H NMR (400 MHz, CD2Cl2) 2.81 (s, 3H), 3.95 (s, 3H), 6.83 (d, 2H), 7.41-7.51 (m, 4H), 7.85 (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-433edc85f03a4c1597fc32911a8c0d4e
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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