HCID 86735531, compound → HCID 66776671, compound

HRID 1679145Notes

Reaction equation

HRID 1679145 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:22]([O-])=O)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([NH2:22])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 86735531HCID 86735531, compound

Product 1

HCID 66776671HCID 66776671, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

The dinitro derivative from Example 1 (10g) was dissolved in glacial acetic acid (1.51) and refluxed. To the refluxing solution, stannous chloride dihydrate (50g) in 50ml of concentrated hydrochloric acid was slowly added over fifteen minutes. After the addition was complete, the reflux was continued for another fifteen minutes. Upon cooling, a dark grey precipitate appeared. This was filtered off, washed with water, boiled in 100ml of 20% aqueous sodium hydroxide and washed with water again. During the washing process, the precipitate turned from grey to orange. To further purify the material, it was refluxed in pyridine with decolorizing charcoal, filtered through Whatman No. 2 paper, and was crystallized from 40% aqueous pyridine. Analysis proved the material to be 4,4'-diamino-p-terphenyl.

Workup

  1. temperaturerefluxed
  2. additionAfter the addition
  3. waitthe reflux was continued for another fifteen minutes
  4. temperatureUpon cooling
  5. filtrationThis was filtered off
  6. washwashed with water
  7. washwashed with water again
  8. customTo further purify the material, it
  9. temperaturewas refluxed in pyridine with decolorizing charcoal
  10. filtrationfiltered through Whatman No
  11. custom2 paper, and was crystallized from 40% aqueous pyridine

Sources & evidence

ORD record
ord-063519c7f8bb4b7e99f8b37ee3bd780d
Source dataset
uspto-grants-1978_03
Patent number
US04079082

Reaction notes

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