Sodium Hydroxide → HCID 19878937, compound

HRID 1885513Notes

Reaction equation

HRID 1885513 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=1[Cl:20])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=1[Cl:20]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 19878934HCID 19878934, compound

Product 1

HCID 19878937HCID 19878937, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-Amino-2',4,4',5,5'-pentachlorobiphenyl was prepared from 2-Nitro-2',4,4',5,5'-pentachlorobiphenyl (2.5 g, 6.8 mmol) by dissolving the compound in acetic acid (60 mL) heated to 100° C. and adding a solution of SnCl2 (6 g) in concentrated HCl (30 mL). The temperature was raised to reflux for 3 h, then the reaction mixture was allowed to cool to ambient temperature, whereupon it was poured into ice (100 g). The pH of the solution was adjusted to 9 with NaOH and then extracted with methylene chloride (2×100 mL). The extract was washed with NaOH (1N, 2×25 mL) and water (100 mL); dried over MgSO4 and filtered to give the impure amine. The crude product was chromatographed in two equal batches (Chromatotron®, Harrison Research, Palo Alto, Calif., 4 mm silica gel, step gradient from hexanes to 10% ethyl acetate in hexanes, 20 mL/min) to give the title hapten (830 mg). Mass spectrum: m/z at 340 (M+1) for C12H6Cl5N.

Workup

  1. temperatureThe temperature was raised
  2. temperatureto reflux for 3 h
  3. temperatureto cool to ambient temperature, whereupon it
  4. extractionextracted with methylene chloride (2×100 mL)
  5. washThe extract was washed with NaOH (1N, 2×25 mL) and water (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5d1f58d5d03044d6b4dd1c574ce8bbf0
Source dataset
uspto-grants-1992_09
Patent number
US05145790

Reaction notes

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