4-Isopropylphenol → HCID 12675962, compound

HRID 929450Notes

Reaction equation

HRID 929450 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:16][CH:15]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 74654-IsopropylphenolHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 12675962HCID 12675962, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following procedure A, 2-chloro-5-nitropyridine (303 mg, 1.91 mmol, 1.00 eq) and 4-iso-propylphenol (331 mg, 2.43 mmol, 1.27 eq) were dissolved in DMF (6.0 mL). Anhydrous K2CO3 (398 mg, 2.88 mmol, 1.51 eq) was added and the reaction mixture was stirred at room temperature for 24 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 pale yellow solid (490 mg, 1.90 mmol, 99% yield). Rf=0.40 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C14H15N2O3+ [M+H]+ 259.1077. found: 259.1072. 1H NMR (400 MHz, CDCl3) δ 9.04 (d, J=3.4 Hz, 1H, aromatic H), 8.44 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.37-7.28 (m, 2H, aromatic H), 7.12-7.06 (m, 2H, aromatic H), 7.03-6.97 (m, 1H, aromatic H), 2.96 (hept, J=6.9 Hz, 1H, CH(CH3)2), 1.30 (d, J=7.0 Hz, 6H, CH(CH3)2). 13C NMR (101 MHz, CDCl3) δ 167.08, 150.67, 146.49, 145.02, 140.18, 134.81, 127.84, 121.11, 111.24, 33.62, 24.03.

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-2c8e3ff59d1044c4b13833d40d7768ef
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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