Methanol → HCID 68698409, compound

HRID 2092503Notes

Reaction equation

HRID 2092503 reaction equation
[F:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].CO>C([O-])(O)=O.[Na+].[Fe]>[NH2:14][C:10]1[CH:9]=[C:8]([C:2]([F:1])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68699432HCID 68699432, compound

Product 1

HCID 68698409HCID 68698409, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

Methyl 2-fluoro-2-(3-nitrophenyl)propanoate (1.0 g, 4.5 mmol) was added by portion to a suspension of Fe in a mixture of 1:5:0.05H2O/MeOH/37% HCl (50 ml). The solution was refluxed for 1 hour. After cooling at room temperature, the reaction mixture was diluted with a saturated solution of NaHCO3 (50 ml), trasferred into a separator funnel and extracted with EtOAc (3×100 mL), dried over Na2SO4 and evaporated under vacuum to give pure methyl 2-(3-aminophenyl)-2-fluoropropanoate as a yellow oil (0.81 g, yield 91%). 1H-NMR (CDCl3) δ 7.15 (t, 1H, J=7 Hz), 6.85-6.75 (m, 2H), 6.75 (t, 1H, J=7 Hz), 3.80 (bs, 3H+NH2), 1.95 (d, 3H, J=23 Hz).

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. customtrasferred into a separator funnel
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-e043bbdd7bfa457a9429ceb5ed6917e3
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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