3-Fluoro-4-nitroanisole → 2-Fluoro-4-methoxyaniline

HRID 1725336Notes

Reaction equation

HRID 1725336 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

3

Reactant 1

HCID 5656543-Fluoro-4-nitroanisole

Product 1

HCID 37563832-Fluoro-4-methoxyanilineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 g (0.175 mole) of 3-fluoro-4-nitroanisole was dissolved in 100 mL of ethanol and degassed several times from alternating vacuum/N2. 1.5 g of Pd/C was added and the contents were hydrogenated using a Parr shaker (35 psi). After 30 min. the pressure had dropped to 5 psi, so it was increased to 35 psi and allowed to react for another 2 hrs. No further pressure drop was experienced. Contents were degassed, filtered through Celite and rotoary-evaporated to dryness to give 23.4 g (95%) of desired product. No purification was necessary. 1H NMR (CDCl3, 400 MHz) 6.71 (dd, 1H), 6.62 (d, 1H), 6.53 (d, 1H) 3.73 (s, 3H), 3.43 (bs, 2H).

Workup

  1. customdegassed several times
  2. addition1.5 g of Pd/C was added
  3. additionAfter 30 min. the pressure had dropped to 5 psi, so it
  4. temperaturewas increased to 35 psi
  5. customto react for another 2 hrs
  6. customContents were degassed
  7. filtrationfiltered through Celite
  8. customrotoary-evaporated to dryness

Sources & evidence

ORD record
ord-a09592b7bccd47fda51bdc1f7c8b5bbf
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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