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

HRID 13528Notes

Reaction equation

HRID 13528 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-89304fd822a1451388c0a7b86ebe9de9
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

Loading…