Triethylamine → HCID 10610748, compound

HRID 1952872Notes

Reaction equation

HRID 1952872 reaction equation
[CH2:1]([C:3]1[CH:16]=[C:15]2[C:6]([NH:7][C:8]3[C:9]([C:18]([OH:20])=[O:19])=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]2=O)=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.[Al]>CCO.Cl[Hg]Cl>[CH2:1]([C:3]1[CH:16]=[C:15]2[C:6]([N:7]=[C:8]3[C:13](=[CH:14]2)[CH:12]=[CH:11][CH:10]=[C:9]3[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5359268AluminumHCID 10754295HCID 10754295, compound

Product 1

HCID 10610748HCID 10610748, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of the above acridone acid (1.00 g, 3.75 mmol) in 50% aqueous EtOH was stirred and heated, then sufficient triethylamine added to obtain a clear yellow solution. Portions of aluminium foil (0.83 g) were amalgamated in a solution of HgCl2 (3 g) in EtOH, then added to the above vigorously boiling solution over 30 min. After the reaction was observed to be complete by tlc, the reaction mixture was filtered and the solids collected were washed with a solution of KOH in aqueous EtOH. The filtrate was then strongly acidified with concentrated HCl and treated with FeCl3 under reflux for 45 min. The reaction mixture was concentrated under reduced pressure and sufficient potassium acetate added until the pH was neutral. Crystallization of the product occurred upon cooling and filtration and recrystallisation of the resulting brown solid gave 7-ethylacridine-4-carboxylic acid (0.77 g, 82%), mp (acetone) 210-211.5° C. 1H NMR [(CD3)2SO] δ 1.35 (t, J=7.5 Hz, 3 H, CH3), 2.91 (q, J=7.5 Hz, 2 H, CH2), 7.83 (dd, J=8.3, 7.2 Hz, 1 H, H-2), 7.97 (dd, J=9.0. 1.9 Hz, 1 H, H-6), 8.09 (br s, 1 H, H-8), 8.26 (d, J=9.0 Hz, 1 H, H-5), 8.54 (dd, J=8.4, 1.2 Hz, 1 H, H-1), 8.71 (br d, J=7.0 Hz, 1 H, H-3), 9.43 (s, 1 H, H-9), 17.09 (br s, 1 H, COOH). Anal. (C16H13NO2) C, H, N.

Workup

  1. temperatureheated
  2. customto obtain a clear yellow solution
  3. additionadded to the above vigorously boiling solution over 30 min
  4. filtrationthe reaction mixture was filtered
  5. customthe solids collected
  6. washwere washed with a solution of KOH in aqueous EtOH
  7. additiontreated with FeCl3
  8. temperatureunder reflux for 45 min
  9. concentrationThe reaction mixture was concentrated under reduced pressure and sufficient potassium acetate
  10. additionadded until the pH
  11. customCrystallization of the product
  12. temperatureupon cooling
  13. filtrationfiltration and recrystallisation of the resulting brown solid

Sources & evidence

ORD record
ord-15321bbd83194ddf8bc8b2c895cf9afc
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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