Pyridine → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzene-1,2-diamine

HRID 13526Notes

Reaction equation

HRID 13526 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].Cl.NO.N1C=CC=CC=1>C(O)C>[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

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 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

A 50 mL round bottom flask was charged with 1 (680 mg, 2.5 mmol), hydroxylamine HCl (191 mg, 2.75 mmol), pyridine (0.25 mL, 3.0 mmol) and ethanol (10 mL). The resulting reaction mixture was stirred at rt overnight. The crude product was concentrated, absorbed onto silica gel, and purified by flash chromatography (97:3 CH2Cl2/MeOH to give 2 as an orange solid. LCMS m/z 289.2 (MH+), tR=2.06 min.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe crude product was concentrated
  3. customabsorbed onto silica gel
  4. custompurified by flash chromatography (97:3 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-e256aff240d2401a9eccdcd5e909d102
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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