Potassium Carbonate → Tert-butyl [3-(3-amino-4-nitrophenoxy)phenyl]carbamate

HRID 2190496Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.F[C:17]1[CH:18]=[CH:19][C:20]([N+:24]([O-:26])=[O:25])=[C:21]([CH:23]=1)[NH2:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[NH2:22][C:21]1[CH:23]=[C:17]([CH:18]=[CH:19][C:20]=1[N+:24]([O-:26])=[O:25])[O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl (3-hydroxyphenyl)carbamate (6.89 g, 32.9 mmol) and 5-fluoro-2-nitroaniline (5.09 g, 32.6 mmol) in N,N-dimethylformamide (100 mL) was added potassium carbonate (11.2 g, 80.9 mmol), and the mixture was vigorously stirred at 100° C. for 14 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (125 ml) and hexane (125 mL), washed with water (150 mL×2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate/hexane=2/98→30/70) to give the title compound (7.7 g, 69%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with water (150 mL×2) and saturated brine (100 mL)
dry with materialsuccessively, and dried over anhydrous magnesium sulfate
filtrationThe insoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-d7477199369342ce9c2a8186166303dd
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324395B2

Reaction notes

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