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

HRID 1915705Notes

Reaction equation

HRID 1915705 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.O(N)C.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 521874O-Methylhydroxylamine 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 25 mL round bottom flask was charged with a suspension of 1 (600 mg, 2.2 mmol), methoxylamine HCl (202 mg, 2.42 mmol), and pyridine (0.22 mL, 2.6 mmol) in ethanol (9 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 303.2 (MH+), tR=2.40 mm.

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-a69bf5bdac2343ed806a51e542955c92
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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