Hydrochloric Acid → HCID 67021636, compound

HRID 1661017Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][C:13](=[O:24])[CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([NH2:22])=[CH:17][C:16]=1[Cl:23].Cl.O1CCOCC1>CO.O1CCOCC1>[CH3:11][O:12][C:13](=[O:24])[CH2:14][C:15]1[C:16]([Cl:23])=[CH:17][C:18]([NH:22][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:19][C:20]=1[Cl:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-3-nitro-pyridine (5.0 g, 31.4 mmol), (4-amino-2,6-dichloro-phenyl)-acetic acid methyl ester (7.8 g 33.3 mmol), and a 4 N solution of HCl in dioxane (12 mL, 48.0 mmol, 2.9 equiv) in MeOH/dioxane (60 mL; 1:1, v/v) is stirred for 46.5 h at 100° C. The reaction mixture is allowed to cool to rt and concentrated in vacuo. The residue is dissolved in EtOAc, washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. Purification of the crude product by silica gel column chromatography (Hexane/EtOAc, 4:1), followed by trituration in diethyl ether, provides the title compound: ES-MS: 355.9/357.9 [M+H]+; tR=5.33 min (System 1); Rf=0.25 (Hexane/EtOAc, 4:1).

Workup

temperatureto cool to rt
concentrationconcentrated in vacuo
dissolutionThe residue is dissolved in EtOAc
washwashed with a saturated aqueous solution of NaHCO3
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customPurification of the crude product by silica gel column chromatography (Hexane/EtOAc, 4:1)

Sources & evidence

ORD record: ord-7409b2574e4c4e9ba1726edb34ca2689
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030311B2

Reaction notes

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