Ethanol → 5-Fluoro-3-nitrobenzene-1,2-diamine

HRID 53802Notes

Reaction equation

HRID 53802 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.CCO>O>[NH2:6][C:5]1[C:4]([N+:12]([O-:14])=[O:13])=[CH:3][C:2]([F:1])=[CH:8][C:7]=1[NH2:9]

Participants

4

Reactant 2

HCID 702EthanolHCID 3453624-Fluoro-2,6-dinitroaniline

Product 1

HCID 154290905-Fluoro-3-nitrobenzene-1,2-diamineYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-fluoro-2,6-dinitroaniline (125 mg, 0.62 mmole) in freshly prepared 6% (NH4)2S (5 mL) and EtOH (5 mL) was refluxed for 30 min, diluted with water (10 mL) and kept at 4° C. for several hours. The precipitate was collected and washed with cold water (2×1 mL), affording 53 mg of 1,2-diamino-4-fluoro-6-nitrobenzene (50%) as red crystals. 1H NMR (CDCl3 : δ 3.619 (s, 2H), 5.724 (s, 2H), 6.732 (dd, 1H, J1 =2.4 Hz, J2 =8.4 Hz), 7.403 (dd, 1H, J1 =2.4 Hz, J2 =8.4 Hz).

Workup

  1. waitkept at 4° C. for several hours
  2. customThe precipitate was collected
  3. washwashed with cold water (2×1 mL)

Sources & evidence

ORD record
ord-43b69cf8b0a442ff8fec982c5271049f
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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