Hydrazine hydrate (1:1) → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzene-1,2-diamine

HRID 13531Notes

Reaction equation

HRID 13531 reaction equation
O.NN.[F:4][C:5]1[C:10]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:9][CH:8]=[C:7]([N+:18]([O-])=O)[C:6]=1[NH2:21]>C(O)C>[F:4][C:5]1[C:10]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:9][CH:8]=[C:7]([NH2:18])[C:6]=1[NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)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 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.13 mL, 2.7 mmol) was added to a solution of phthalimide 1 (134 mg, 0.39 mmol) in ethanol (4 mL). The reaction was maintained overnight at rt and then was filtered through Celite. The filter cake was rinse with EtOAc (3×) and the organic portions were combined and concentrated to give diamine 2 which was carried forward without further purification: LCMS m/z 215.1 (MH+), tR=1.77 min.

Workup

  1. filtrationwas filtered through Celite
  2. washThe filter cake was rinse with EtOAc (3×)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d971abec845546ceb29973a910666f51
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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