4-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroaniline → 4-Fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

HRID 2274413Notes

Reaction equation

HRID 2274413 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][C:5]([NH2:15])=[C:4]([N+:16]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 5366794-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 106567604-Fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

21.2 g of 4-fluoro-5-(4-methylpiperazin-1-yl)-2-nitrophenylamine in solution in 800 mL of methanol are hydrogenated under 1 bar of hydrogen pressure in the presence of 2.1 g of palladium-on-charcoal at 25° C. for 16 hours. The reaction crude is filtered through celite and the filtrate is concentrated under vacuum in a rotary evaporator. 18.7 g of 4-fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine in the form of a black oil are isolated. 1H NMR (400 MHz, DMSO-d6, δ in ppm), for this batch, all the signals are broad with: 2.19 (s, 3H); 2.40 (m, 4H); 2.79 (m, 4H); 4.22 (s, 2H); 4.31 (s, 2H); from 6.24 to 6.33 (m, 2H). EI mass spectrum: m/z=224: M+. (base peak)—m/z=209: (M—CH3)+—m/z=153: (M−C4H9N)+—m/z=70: C4H8N+—m/z=43: C2H5N+.

Workup

  1. customThe reaction crude
  2. filtrationis filtered through celite
  3. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator

Sources & evidence

ORD record
ord-7c2d0087dfa644bdb30087601d2ac64f
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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