Water → 4-[(6-Chloropyrimidin-4-yl)oxy]-2-fluoroaniline

HRID 492860Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=2)[N:5]=[CH:4][N:3]=1.O.[Cl-].[NH4+]>C(O)C.CN(C)C=O.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)=[CH:10][C:11]=1[F:18]

Participants

Conditions

Temperature: 100 °C

Procedure

After dissolving 4-chloro-6-(3-fluoro-4-nitrophenoxy)pyrimidine (9.726 g) in ethanol (100 ml)-N,N-dimethylformamide (100 ml) at room temperature, water (50 ml), ammonium chloride (20 g) and electrolytic iron powder (10 g) were added and the mixture was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature. The insoluble portion was removed using celite prior to washing with ethyl acetate. The filtrate was concentrated under reduced pressure, and then the residue was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine in that order and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was dried under reduced pressure to provide the title compound (8.204 g, 95%) as pale yellow crystals.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe insoluble portion was removed
washto washing with ethyl acetate
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was partitioned between ethyl acetate and water
washThe separated organic layer was washed with water and brine in that order
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe residue was dried under reduced pressure

Sources & evidence

ORD record: ord-c23795f5ff5e4e64b80360de2a1a51c4
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531532B2

Reaction notes

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