4-Chloro-2-nitrophenol → HCID 89611067, compound

HRID 869052Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1.Cl.Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23]>CN(C=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium carbonate (3.2 g, 12.3 mmol) was added to a solution of 4-chloro-2-nitro-phenol (6.0 g, 34.6 mmol) in DMF (60 mL). The mixture was cooled to 0° C. 2-Chloro-N,N-dimethyl ethyl amine hydrochloride (9.96 g, 69.1 mmol) was added in portions. The reaction mixture was allowed to warm to rt, stirred for 4 h, heated to 95° C., stirred for 16 h, allowed to cool to rt, quenched by addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/MeOH, 98:2) to provide 3.0 g of the title compound. tR: 0.12 min (LC-MS 2); ESI-MS: 245 [M+H]+ (LC-MS 2); Rf=0.29 (CHCl3/MeOH, 9:1).

Workup

temperatureto warm to rt
temperatureheated to 95° C.
stirringstirred for 16 h
temperatureto cool to rt
customquenched by addition of a saturated aqueous solution of ammonium chloride
extractionextracted with EtOAc
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (CHCl3/MeOH, 98:2)

Sources & evidence

ORD record: ord-fb660586052e4c7d9c4c94c612b3d2fb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969341B2

Reaction notes

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