Water → HCID 59437335, compound

HRID 657071Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[Na].Cl[C:13]1[N:18]=[C:17]([NH2:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:13]2[N:18]=[C:17]([NH2:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-Methoxybenzyl alcohol (4.8 g, 34.7 mmol) was added to sodium (0.8 g, 34.7 mmol) in toluene (100 mL). After most of the sodium has dissolved 6-chloro-3-nitro-2-pyridineamine (5 g, 28.9 mmol) was added and the reaction was heated at 120° C. for 4 h. As there was still some starting material left, more anion of the 4-methoxybenzyl alcohol was prepared in a separate flask (0.6 g of sodium in 30 mL of toluene and 4 g of 4-methoxybenzyl alcohol were used) and added to the reaction at room temperature. The reaction was then stirred at room temperature for 5 h then water (250 mL) was added and the volume reduced to 200 mL. Diethyl ether was then added and the aqueous phase was extracted (3×500 mL). The combined organic phases were dried (MgSO4), filtered and evaporated. The residue was then chromatographed on silica gel, eluting with DCM to afford 4.8 g of the title compound (60%).

Workup

additionwas added
waitleft
additionadded to the reaction at room temperature
extractionthe aqueous phase was extracted (3×500 mL)
dry with materialThe combined organic phases were dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was then chromatographed on silica gel
washeluting with DCM

Sources & evidence

ORD record: ord-523f514491074777b7c3242933589182
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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