Methanol → 4-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroaniline

HRID 1004576Notes

Reaction equation

HRID 1004576 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH:12]2C)=[CH:6][C:5]=1[NH:18]C(=O)C)([O-:3])=[O:2].[OH-].[Na+].O.[CH3:25]O>>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[CH2:12][CH2:13][N:14]([CH3:25])[CH2:15][CH2:16]2)=[CH:6][C:5]=1[NH2:18])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 18792798N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide

Product 1

HCID 5366794-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroanilineYield 75%

Procedure

The acetamide (25.0 g, 0.085 mol) (obtained in step 1 above) was dissolved in methanol (160 mL) and 6 M NaOH solution (42 nL) was added dropwise at ca 30° C. and stirred for 6 h. The mixture was cooled in an ice bath and water (300 mL) was added dropwise. The resultant precipitate was collected by filtration and dried to yield 2-nitro-4-fluoro-5-(4-methylpiperazin-1-yl)aniline (16.0 g, 75%) as a brown solid. mp 154-155° C.; IR (KBr) 3383, 1247 cm-1 ; 1H NMR (CDCl3 ) δ 2.32 (s, 3H, CH3), 2.54 (t, J=5.0 Hz, 4H, N(CH2)2), 3.24 (t, J=4.6 Hz, 4H, N(CH2)2, 6.02 (d, J=7.5 Hz, 1H), 6.12 (brs, 2H, NH2), 7.74 (d, J=14.0 Hz, 1H); Mass (m/z) 254 (M+.).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationThe resultant precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-b4254193d65f46c7b87d0a8e5962ac4a
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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