Methanol → (2-amino-4-fluorophenyl)-N-(1-methylethyl)-methylamine

HRID 583073Notes

Reaction equation

HRID 583073 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH:13]([NH2:16])([CH3:15])[CH3:14].[CH3:17]O>[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[N:16]([CH3:17])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 6363IsopropylamineHCID 762264-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 17777166(2-amino-4-fluorophenyl)-N-(1-methylethyl)-methylamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4-fluoro-2-nitro benzaldehyde (3.76 g, 25 mmol) in dry MeOH (120 ml), was added isopropyl amine (2.1 ml, 25 mmol) and the mixture stirred for 2 hours at room temperature in Argon atmosphere. Then it was then transferred into a Parr bottle containing 5% Pd on charcoal (246 mg) under Argon and hydrogenated at 30 psi for 18 hours. The suspension was filtered over a celite pad, washed with MeOH and evaporated at reduced pressure to afford (2-amino-4-fluorophenyl)-N-(1-methylethyl)-methylamine as a yellow oil.

Workup

  1. waithydrogenated at 30 psi for 18 hours
  2. filtrationThe suspension was filtered over a celite pad
  3. washwashed with MeOH
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-6c924382919a405cbb3d6a693f7e8699
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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