Methanol → Methyl 6-(3-aminophenyl)-6-(3-pyridyl)hex-5-enoate

HRID 374826Notes

Reaction equation

HRID 374826 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:8]=[CH:9][CH:10]=1)(=O)C.[CH3:25]O>Cl>[NH2:4][C:5]1[CH:6]=[C:7]([C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:25])=[O:17])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 537920006-(3-Acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid

Product 1

HCID 53766536Methyl 6-(3-aminophenyl)-6-(3-pyridyl)hex-5-enoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

65 g of 6-(3-acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid are refluxed for 4 hours in a mixture of 400 ml of methanol and 200 ml of methanolic hydrochloric acid. The solvent is removed and the residue is taken up in water. The aqueous phase is washed with ethyl acetate and adjusted to pH 8-9 by the addition of 4N sodium hydroxide solution. The aqueous phase is extracted with ethyl acetate. The organic phase is washed, dried and evaporated down.

Workup

  1. customThe solvent is removed
  2. washThe aqueous phase is washed with ethyl acetate
  3. additionadjusted to pH 8-9 by the addition of 4N sodium hydroxide solution
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. washThe organic phase is washed
  6. customdried
  7. customevaporated down

Sources & evidence

ORD record
ord-0859a01df32a403abec923827986093b
Source dataset
uspto-grants-1996_01
Patent number
US05482948

Reaction notes

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