Acetic Acid → HCID 67923401, compound

HRID 1084442Notes

Reaction equation

HRID 1084442 reaction equation
[CH3:1][N:2]1[C:11](/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:25].C(O)(=O)C.Cl>O>[CH3:1][N:2]1[C:11](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[C:10]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 86744703HCID 86744703, compound

Product 1

HCID 67923401HCID 67923401, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl (E)-3-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)propenoate (4.0 g) in a mixture of glacial acetic acid (50 ml) and concentrated hydrochloric acid (50 ml) was heated at reflux for 2 hours and then poured onto a mixture of ice and water (100 g). The resulting white solid was filtered off and crystallised from ethanol, to give (E)-3-(2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)propenoic acid (2.8 g) in the form of white crystals, m.p.266°-268° C. [Elemental analysis: C,74.3; H,5.0; N,4.2%; calculated: C,74.7; H,4.95; N,4.59%].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe resulting white solid was filtered off
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-65a8724fc18a4553a30f4f6bf07acf93
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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