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

HRID 2070337Notes

Reaction equation

HRID 2070337 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.CCOC(C)=O>[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, compoundYield 188.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A 250 mL sealed tube was charged with benzyl alcohol 1 (1.0 g, 3.6 mmol), MnO2 (4.7 g, 54 mmol) and EtOAc (20 mL). The resulting suspension was heated to 120° C. with stirring for 2 hours. Reaction mixture filtered through Celite and washed successively with EtOAc, MeOH, and EtOH. Organics evaporated to give 936 mg (3.4 mmol, 94%) of 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, 1 H), 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. customA 250 mL sealed tube
  2. customReaction mixture
  3. filtrationfiltered through Celite
  4. washwashed successively with EtOAc, MeOH, and EtOH
  5. customOrganics evaporated

Sources & evidence

ORD record
ord-e3e896be3b704b22befc19755c11983f
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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