Acetic Acid → HCID 19002353, compound

HRID 1742884Notes

Reaction equation

HRID 1742884 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:6]([CH:8]([CH2:14][CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.C([O-])(=O)C.[NH4+:33].C(O)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:33]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 19002344HCID 19002344, compound

Product 1

HCID 19002353HCID 19002353, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-(3,4-dimethoxybenzoyl)-5-oxo-5-phenylvalerate (compound no. 314; 7.7 g; 0.02 mole), ammonium acetate (3.1 g; 0.04 mole) and acetic acid (30 ml) is heated to reflux temperature for 4 hours. The reaction medium is poured into water (300 ml): an oil is released. The latter is extracted with ethyl acetate (200 ml). The organic solution is washed with water (3×100 ml), then dried over anhydrous magnesium sulphate and concentrated under reduced pressure. A light brown oil (4.5 g; yield: 62%) is obtained which corresponds to ethyl 2-(3,4-dimethoxyphenyl)-6-phenylnicotinate.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature for 4 hours
  3. extractionThe latter is extracted with ethyl acetate (200 ml)
  4. washThe organic solution is washed with water (3×100 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d503ddb886140f5af965da22870dbd8
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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