Potassium Carbonate → HCID 89647780, compound

HRID 929442Notes

Reaction equation

HRID 929442 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:19][CH:20]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154204-ButylphenolHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 89647780HCID 89647780, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following procedure A, 2-chloro-5-nitropyridine (103 mg, 0.65 mmol, 1.00 eq) and 4-butylphenol (126 mg, 0.84 mmol, 1.29 eq) were dissolved in DMF (2.5 mL). Anhydrous K2CO3 (143 mg, 1.04 mmol, 1.59 eq) was added and the reaction mixture was stirred at room temperature for 6 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100) to afford the title compound as colourless solid (190 mg, 0.70 mmol, quant. yield). Rf=0.33 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C15H17N2O3+ [M+H]+ 273.1234. found: 273.1226. 1H NMR (400 MHz, CDCl3) δ 9.05 (dd, J=2.9, 0.6 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.32-7.21 (m, 2H, aromatic H), 7.11-7.02 (m, 2H, aromatic H), 7.00 (dd, J=9.0, 0.6 Hz, 1H, aromatic H), 2.69-2.60 (m, 2H, Ar—CH2CH2CH2CH3), 1.70-1.57 (m, 2H, Ar—CH2CH2CH2CH3), 1.39 (dq, J=14.6, 7.3 Hz, 2H, Ar—CH2CH2CH2CH3), 0.95 (t, J=7.3 Hz, 3H, Ar—CH2CH2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 167.27, 150.75, 145.22, 140.86, 140.30, 134.92, 129.91, 121.22, 111.32, 35.21, 33.67, 22.51, 14.08.

Workup

  1. extractionAfter extraction with Et2O
  2. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100)

Sources & evidence

ORD record
ord-c62b2ade7f4741bd9c8fe17c17b4f13c
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

Loading…