Isopropanol → 2-Isopropoxy-5-nitropyridine

HRID 657232Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.CN(C=O)C.[H-].[Na+].[CH:18]([OH:21])([CH3:20])[CH3:19]>>[CH:18]([O:21][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)([CH3:20])[CH3:19]

Participants

Reactant 4

HCID 3776Isopropanol

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 120361742-Isopropoxy-5-nitropyridine

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-nitro-pyridine (450 mg, 2.84 mmol) in isopropanol (10 mL)/DMF (7 mL) was added 60% NaH (57 mg). The mixture was stirred at 80° C. for 4 h and the organic solvents were evaporated under reduced pressure. The residue was partitioned between EtOAc and water. The EtOAc extracts were dried (Na2SO4) and evaporated. The crude product was used for the next step reaction without further purification. 1H NMR (300 MHz, CDCl3) δ 9.06 (d, J=2.81 Hz, 1H), 8.32 (dd, J=8.79 and 2.53 Hz, 1H), 6.74 (d, J=8.61 Hz, 1H), 5.43 (m, 1H), 1.38 (d, J=6.20 Hz, 6H).

Workup

customthe organic solvents were evaporated under reduced pressure
customThe residue was partitioned between EtOAc and water
dry with materialThe EtOAc extracts were dried (Na2SO4)
customevaporated
customThe crude product was used for the next step reaction without further purification

Sources & evidence

ORD record: ord-ea2fe15a6b764515825a433bf78ef39f
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071768B2

Reaction notes

Loading…