Ammonium Chloride → HCID 59266537, compound

HRID 1043434Notes

Reaction equation

HRID 1043434 reaction equation
[Cl-].[NH4+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]([O:21][CH3:22])=[O:20])=[CH:12][C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=2)=[CH:6][CH:5]=1>CO.[Zn]>[NH2:16][C:13]1[CH:12]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[C:10]([C:7]2[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 18526013Methyl 4′-bromo-4-nitro[1,1′-biphenyl]-2-carboxylate

Product 1

HCID 59266537HCID 59266537, compoundYield 119%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Ammonium chloride (11.5 g, 214 mmol) and zinc (14.0 g, 214 mmol) were added to a solution of methyl 4′-bromo-4-nitrobiphenyl-2-carboxylate (7.2 g, 21.42 mmol) in MeOH (110 mL) and stirred at room temperature for 1 hour. The solid was filtered, and the filtrate was evaporated. The residue was dissolved in diethyl ether, filtered and concentrated to give methyl 4-amino-4′-bromobiphenyl-2-carboxylate (7.8 g, 25.5 mmol, 119% yield). LCMS: rt=1.54 min, [M+H]+=305 and 307; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in diethyl ether
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd058a3e22b4441b8146f3b32e2117d
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

Loading…