Water → N-(2-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine

HRID 1942156Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:2]1=2.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:11][C:8]1[CH:9]=[CH:10][C:2]2[O:1][CH2:6][CH2:5][O:4][C:3]=2[CH:7]=1)([O-:21])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

5.9 g (39 mmol) of 2,3-dihydrobenzo[b]1,4-dioxin-6-amine and 5.0 g (35 mmol) of 2-fluoronitrobenzene were dissolved in N-methylpyrrolidone (70 mL) and 20.8 g (150 mmol) of potassium carbonate was added thereto. The solvent was heated with stirring for 10 hours at 120° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The extracted organic layer was washed with water, 10% hydrochloric acid, water, and a saturated aqueous solution of sodium chloride in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:4), to obtain 6.4 g (yield: 66%) of N-(2-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine as a red liquid.

Workup

temperatureThe solvent was heated
extractionextracted with ethyl acetate
washThe extracted organic layer was washed with water, 10% hydrochloric acid, water
dry with materiala saturated aqueous solution of sodium chloride in this order, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue thus obtained
customwas purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:4)

Sources & evidence

ORD record: ord-f72c2662c17f43eba5f06c1bdefeea5c
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389523B2

Reaction notes

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