Benzoic Acid → HCID 20440411, compound

HRID 1633258Notes

Reaction equation

HRID 1633258 reaction equation
O1[CH2:20][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH2:14][C:15](OCC)=[O:16].[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[NH:29][CH2:30][CH2:31][NH2:32].[H][H].[C:35]([OH:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CC(O)C.[Pd].C(O)(=O)C.CO>[C:35]([O:43][CH:2]([CH2:20][NH:32][CH2:31][CH2:30][NH:29][C:23]1[C:22]([CH3:21])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:28])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[CH2:14][C:15](=[O:16])[NH:11]2)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

9

Reactant 4

HCID 243Benzoic AcidHCID 12666312N-(2,6-dimethylphenyl)-ethylenediamineHCID 13340510HCID 13340510, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20440411HCID 20440411, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

11.3 g. Ethyl [2-(2,3-epoxypropoxy)-6-nitrophenyl]-acetate (see Federal Republic of Germany Patent Specification No. 29 058 762) and 13.1 g 2-(2,6-dimethylphenylamino)-ethylamine (0.08 mol) in 100 ml. methanol are left to stand for 2 days at ambient temperature. 100 ml. Acetic acid and 1 g. 10% palladium-charcoal are then added thereto, followed by hydrogenation at a hydrogen pressure of 1 bar. After filtering off the catalyst, the filtrate is distilled in a vacuum and the residue remaining behind is dissolved in water. The base is precipitated out by adding an aqueous solution of potassium carbonate and extracted with ethyl acetate. After drying the extract over anhydrous sodium sulfate and evaporating the organic phase, there are obtained 7.2 g. of crude product. By dissolving this in propan-2-ol and adding the calculated amount of benzoic acid, there are obtained 4.3 g. (21% of theory) of the desired compound; m.p. 191° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. distillationthe filtrate is distilled in a vacuum
  3. dissolutionthe residue remaining behind is dissolved in water
  4. customThe base is precipitated out
  5. additionby adding an aqueous solution of potassium carbonate
  6. extractionextracted with ethyl acetate
  7. customAfter drying the
  8. extractionextract over anhydrous sodium sulfate
  9. customevaporating the organic phase, there
  10. customare obtained 7.2 g
  11. customare obtained 4.3 g

Sources & evidence

ORD record
ord-7fb66a1a9de64cfaa3e161ef3ce79dea
Source dataset
uspto-grants-1984_10
Patent number
US04479962

Reaction notes

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