Isopropanol → (3-Amino-4-fluorophenyl)methanol
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-])=O.C(O)(C)C.[Cl-].[NH4+]>[Fe].O>[NH2:10][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:2]=1[F:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A flask equipped with overhead stirrer was charged with 4-fluoro-3-nitrobenzyl alcohol (20 g, 0.117 mol) and 200 mL of 5:1 isopropanol:water. Ammonium chloride (62 g, 1.17 mol) was added followed by iron filings (65 g, 1.17 mol). The mixture was stirred at 70 C for 1.5H when it was shown to be complete by LC-MS. The liquid was decanted and the solids were washed with additional isopropanol: water. The isopropanol was removed and the residue was diluted with 0.5 N HCl and was extracted with ethyl acetate. The aqueous layer was brought to pH 12-14 with 2.5 N NaOH and was extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated in vacuo. 3-Amino-4-fluorophenyl methanol was isolated as a brown solid (4.5 g, 27%) and was used without further purification. LC/MS, tr=2.40 minutes (5 to 95% acetonitrile/water over 8 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 142 (M+H). ES-HRMS m/z 142.0692 (M+H calcd for C7H8FNO requires 142.0663).
Workup
- customA flask equipped with overhead stirrer
- customThe liquid was decanted
- washthe solids were washed with additional isopropanol
- customThe isopropanol was removed
- additionthe residue was diluted with 0.5 N HCl
- extractionwas extracted with ethyl acetate
- extractionwas extracted with ethyl acetate
- dry with materialThe organic layer was dried with anhydrous Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-187b9493791a4a9d888c26658386e21b
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629363B2
Reaction notes
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