Acetic Acid → HCID 54235086, compound

HRID 652957Notes

Reaction equation

HRID 652957 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=[CH:21][C:22]([NH:24][C:25]2[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:27]([OH:29])=[O:28])=[O:23])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:9]COCCOC.C(O)(=O)C.O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=[CH:21][C:22]([NH:24][C:25]2[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:27]([OH:29])=[O:28])=[O:23])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 54120167HCID 54120167, compound

Product 1

HCID 54235086HCID 54235086, compoundYield 541.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 56 mg (0.12 mmol) of the amide compound prepared above in 1 ml of dioxane was added 4 ml of 80% acetic acid. The mixture was heated under reflux for 2 hours. Water was added to the reaction solution, and crystals then formed were isolated by filtration and recrystallized from methanol. There was obtained 24 mg (0.65 mmol) of N-{5-(3,5-dimethoxy-4-hydroxyphenyl)-2,4-pentadienoyl}anthranilic acid. Spectrophotometric data of the product support the structure shown below. ##STR69##

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customthen formed
  4. customwere isolated by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a9bb2f460d4f49f7939c2485d3ce6a83
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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