Ammonium Chloride → 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

HRID 889507Notes

Reaction equation

HRID 889507 reaction equation
[Cl-].[NH4+].[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([N+:13]([O-])=O)[C:5]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24]>C(O)C.[Fe]>[F:10][C:9]1[C:4]([F:3])=[C:5]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:6]([NH2:13])=[C:7]([O:11][CH3:12])[CH:8]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 593863122,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroaniline

Product 1

HCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ammonium chloride (1.18 g, 20.16 mmol) and iron powder (1.15 g, 21.44 mmol) were added to a stirred solution of (2,3-difluoro-5-methoxy-6-nitro-phenyl)-(2-fluoro-4-iodo-phenyl)-amine (0.57 g, 1.34 mmol) in ethanol (20 mL). The mixture was stirred at reflux for 16 hours, cooled to room temperature, filtered over celite and the filtrate concentrated to dryness. The resulting residue was taken into ethyl acetate, washed with water, dried over sodium sulfate and further purified by crystallization from ethanol to provide the product as an off-white solid (0.47 g, 90.3%). M−H+: 393.2. 1H NMR (DMSO, 300 MHz): 3.76 (s, 3H); 6.1 (t, 1H); 6.8-7.0 (m, 1H); 7.2 (d, 1H); 7.35 (s, 1H); 7.42 (d, 1H).

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationfiltered over celite
  3. concentrationthe filtrate concentrated to dryness
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customfurther purified by crystallization from ethanol

Sources & evidence

ORD record
ord-abfbd37b36244d1b869eb25034e99563
Source dataset
uspto-grants-2012_08
Patent number
US08252842B2

Reaction notes

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