Potassium Carbonate → 4-(4-Methoxyphenyl)-3-nitropyridine

HRID 1783566Notes

Reaction equation

HRID 1783566 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:20]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 122442064-Chloro-3-nitropyridine hydrochloride

Product 1

HCID 153664184-(4-Methoxyphenyl)-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Methoxyphenylboronic acid (24.54 g), 4-chloro-3-nitropyridine hydrochloride (26.24 g), Pd(Ph3P)4 (4 g) and K2CO3 (111 g) were combined in DME (500 mL). The reaction was heated to reflux for 10 hours. After the mixture cooled down to room temperature, it was poured into saturated aqueous NH4OAc (500 mL) solution. The aqueous phase was extracted with EtOAc (3×200 mL). The combined extract was concentrated to give a residue which was purified using silica gel chromatography (10% to 30% EtOAc/PE) to afford 10.6 g of Precursor 1, 3-Nitro-4-(4-methoxyphenyl)pyridine. MS m/z: (M+H)+ calcd for C12H11N2O3: 231.08; found 231.02. HPLC retention time: 1.07 minutes (column B).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 10 hours
  3. extractionThe aqueous phase was extracted with EtOAc (3×200 mL)
  4. extractionThe combined extract
  5. concentrationwas concentrated
  6. customto give a residue which
  7. customwas purified

Sources & evidence

ORD record
ord-96b057b00586404b97355a27251e06af
Source dataset
uspto-grants-2009_03
Patent number
US07501420B2

Reaction notes

Loading…