Hydrochloric Acid → 2-(4-Chlorophenylmethylamino)-5-fluoronitrobenzene

HRID 1493314Notes

Reaction equation

HRID 1493314 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-:22].[K+].[K+].Cl>O1CCCC1.O>[CH:13]([O:22][CH:7]([CH3:6])[CH3:2])([CH3:20])[CH3:14].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 677672,5-Difluoronitrobenzene

Product 2

HCID 7914Diisopropyl EtherHCID 149529762-(4-Chlorophenylmethylamino)-5-fluoronitrobenzeneYield 158.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

30 g of 2,5-difluoronitrobenzene and 26.7 g of 4-chlorobenzylamine are dissolved in 300 ml of tetrahydrofuran. 40 g of potassium carbonate are added to this solution and the mixture is refluxed for 8 hours. After cooling, the reaction mixture is added to 1.7 l of water and 50 ml of concentrated hydrochloric acid. The crystals obtained are filtered off and washed with water and then with isopropyl ether to give 41.9 g of 2-(4-chlorophenylmethylamino)-5-fluoronitrobenzene in the form of crystals melting at 160° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. temperatureAfter cooling
  3. customThe crystals obtained
  4. filtrationare filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-6565ad857e374bc2b327b42e2a1c4edd
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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