Ammonium Chloride → 9-Acridinecarboxylic acid, 9,10-dihydro-10-methyl-, phenyl ester

HRID 2288573Notes

Reaction equation

HRID 2288573 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH3:9][N+:10]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2.[Cl-].[NH4+]>C(O)C.C(Cl)Cl.[Zn]>[CH3:9][N:10]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]([C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 1547628210-Methyl-9-(phenoxycarbonyl)acridin-10-ium trifluoromethanesulfonate

Product 1

HCID 8287619-Acridinecarboxylic acid, 9,10-dihydro-10-methyl-, phenyl ester

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate (10 mg, 0.0216 mmol) was suspended in absolute ethanol (10 mL) and the mixture was refluxed for 15 min to obtain a clear solution. Ammonium chloride (88 mg, 1.6 mmol) was added by portions to the solution followed by zinc (108 mg, 1.6 mmol). Addition of zinc caused the yellow color of the solution to disappear immediately. The colorless solution was refluxed for 2 h. TLC of the reaction mixture showed complete conversion to a non polar material. The solution was filtered and precipitate was washed with ethanol (3×20 mL). The filtrate was concentrated to obtain an off-white solid which was redissolved in CH2Cl2 and washed with water (2×15 mL). The organic layer was dried over Na2SO4 and concentrated to yield the crude product which was purified by preparative TLC using (30% ethyl acetate:hexane). Pure product was obtained as an off-white solid. 1H NMR (CDCl3) δ 3.38 (s, 3H), 5.16 (s, 1H), 6.89-7.37 (m, 13H); 13C NMR (CDCl3) δ 33.29, 49.72, 112.93, 120.19, 121.36, 125.73, 128.67, 129.16, 129.26, 142.37, 151.04, 170.22.

Workup

  1. temperaturethe mixture was refluxed for 15 min
  2. customto obtain a clear solution
  3. temperatureThe colorless solution was refluxed for 2 h
  4. filtrationThe solution was filtered
  5. washprecipitate was washed with ethanol (3×20 mL)
  6. concentrationThe filtrate was concentrated
  7. customto obtain an off-white solid which
  8. washwashed with water (2×15 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a2a37a9ccd804b02aeb6a18d0933f802
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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