1-Methoxy-2-propanol → 5-Chloro-3-(2-methoxy-1-methyl-ethoxy)-2-nitro-pyridine

HRID 1966237Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][CH2:33][CH:34](O)[CH3:35]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH:34]([CH3:35])[CH2:33][O:32][CH3:31])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Chloro-2-nitro-pyridine-3-ol (5.7 mmol) is dissolved in THF (35 ml) and triphenylphosphin (2 eq.) and 1-Methoxy-2-propanol (1 eq.) is added at 0° C. After addition of di-tert.-butylazodicarboxylate (1.5 eq) in THF (10 ml), the reaction is stirred five hours at 0° C. The solvent is removed in vacuo. 5-Chloro-3-(2-methoxy-1-methyl-ethoxy)-2-nitro-pyridine is obtained after column chromatography (heptan/ethylacetate) as yellow solid in a yield of 100%. HPLC (method C): 1.81 min; LC-MS (method A): 1.64 min, 247.05 (MH+).

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-9b6d110d96304d60bf42e7dcd21dd991
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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