2-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzene-1,2-diamine

HRID 13529

Reaction equation

HRID 13529 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([N+:15]([O-])=O)[C:3]=1[NH2:18]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([NH2:15])[C:3]=1[NH2:18]

Participants

4

Reactant 1

HCID 220408162-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

Product 1

HCID 220407433-Fluoro-4-(4-methylpiperazin-1-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A reaction tube was charged with a suspension of 1 (270 mg, 0.9 mmol) and Lindlar catalyst (192 mg, 10 mol %) in methanol (5 mL), and was then placed on a Parr shaker. The was reaction pressurized with H2 (60 psi) and maintained for 1 h. The reaction was filtered through Celite and the remained solids were washed with methanol. The combined organics were concentrated to give 2 as a brown semi-solid which was carried forward without further purification LCMS m/z 273.3 (MH+), tR=1.56 min.

Workup

  1. customThe was reaction
  2. temperaturemaintained for 1 h
  3. filtrationThe reaction was filtered through Celite
  4. washthe remained solids were washed with methanol
  5. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-39232e59ed3b4d1687c551e770f893c2
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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