1-Fluoro-2-nitrobenzene → HCID 18449410, compound

HRID 1270398Notes

Reaction equation

HRID 1270398 reaction equation
C(N(CC)C(C)C)(C)C.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[O:20]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21]1>C(O)CCC>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:25][CH:22]1[CH2:23][CH2:24][O:20][CH2:21]1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 3365553Oxolan-3-amine

Product 1

HCID 18449410HCID 18449410, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
180 °C

Procedure

N,N-Diisopropylethylamine (3.2 mL, 18.4 mmol) was added to a solution of 1-fluoro-2-nitrobenzene (0.484 mL, 4.6 mmol) and (±)-tetrahydrofuran-3-amine (400 mg, 4.6 mmol) in n-butanol (10 mL) and the mixture heated to 180° C. in a microwave reactor. After 20 min, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, gave the title compound. MS: m/z=209 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography
  4. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-6746f8291a82466da450d66928ea3783
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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