2-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine → HCID 22040478, compound

HRID 2070338Notes

Reaction equation

HRID 2070338 reaction equation
F[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]>O=[Mn]=O.C(Cl)(Cl)Cl>[CH:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:7]3[CH:2]=[C:3]([NH2:18])[C:4]([NH2:15])=[CH:5][CH:6]=3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2][CH2:7]1

Participants

4

Reactant 1

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

Product 1

HCID 22040478HCID 22040478, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A 100 mL round bottom flask was charged with benzyl alcohol 1 (1.38 g, 5.0 mmol), MnO2 (6.52 g, 75 mmol) and CHCl3 (20 mL). The resulting suspension stirred at rt overnight. Reaction mixture filtered through Celite, washed successively with CHCl3 and EtOH, and evaporated. Crude product absorbed onto silica gel and chromatographed using 98:2 CH2Cl2/MeOH to give 2 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 10.01 (s, 1H), 8.64 (d, J=5.5 Hz, 1H), 8.09 (br s, 1H), 7.96 (d, J=2.75 Hz, 1H), 7.37 (d, J=2.48 Hz, 1H), 7.29 (d, J=2.75 Hz, 1H), 7.08 (dd, J=2.47, 5.5 Hz, 1H), 6.94 (d, J=9.35 Hz, 1H), 3.08 (d, J=5.23 Hz, 3H).

Workup

  1. customReaction mixture
  2. filtrationfiltered through Celite
  3. washwashed successively with CHCl3 and EtOH
  4. customevaporated
  5. customCrude product absorbed onto silica gel
  6. customchromatographed

Sources & evidence

ORD record
ord-b41b2708814d4927833fd7cca9ce8821
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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