2-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzene-1,2-diamine

HRID 13525Notes

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]>O=[Mn]=O.CCOC(C)=O>[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

Conditions

Temperature: 120 °C

Procedure

A 250 mL reaction tube was charged with benzyl alcohol 1 (1.0 g, 3.6 mmol), MnO2 (4.7 g, 54 mmol) and EtOAc (20 mL). The reaction tube was sealed was heated to 120° C. with stirring for 2 h. The reaction was allowed to cool to rt, then filtered through Celite and washed successively with EtOAc, MeOH, and EtOH. The combine organics were concentrated 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, 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

customA 250 mL reaction tube
customThe reaction tube was sealed
temperatureto cool to rt
filtrationfiltered through Celite
washwashed successively with EtOAc, MeOH, and EtOH
concentrationThe combine organics were concentrated

Sources & evidence

ORD record: ord-87086be8c10c472cbd504bdc13f57b94
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728010B2

Reaction notes

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