Water → HCID 24771073, compound

HRID 1162172Notes

Reaction equation

HRID 1162172 reaction equation
[OH-].[NH4+:2].Cl([O-])(=O)(=O)=O.[F:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:14]4[C:26](=[O:27])[CH2:25][C:24]([CH3:29])([CH3:28])[CH2:23][C:15]=4[O+]=[C:17]([CH3:22])[C:18]=3[NH:19][C:20]=2[CH:21]=1.O>C(O)(C)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:14]4[C:26](=[O:27])[CH2:25][C:24]([CH3:28])([CH3:29])[CH2:23][C:15]=4[N:2]=[C:17]([CH3:22])[C:18]=3[NH:19][C:20]=2[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium Hydroxide2×HCID 178434811HCID 178434811, compound

Product 1

HCID 24771073HCID 24771073, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Aqueous ammonium hydroxide solution (3 mL) was added to a suspension of 9-fluoro-3,3,6-trimethyl-1-oxo-2,3,4,7-tetrahydro-1H-5-oxonia-7-aza-benzo[c]fluorene perchlorate of Example 3b (0.72 g, 1.88 mmol) in isopropanol (2 mL). The reaction mixture was refluxed for 1 h, cooled, and water (5 mL) was added. Aqueous ammonium hydroxide solution was added to the mixture to pH 9. The precipitate was filtered off, washed with water and dried. The crude product was dissolved in acetone, and 37% aqueous hydrochloric acid (0.2 mL) was added. The precipitate was filtered off, suspended in hot water, and the mixture was basicified with ammonium hydroxide to pH 9. The product was filtered off, washed with water, dried and crystallized from toluene to give 0.26 g (50%) of colorless crystals; m.p. 244-246° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. temperaturecooled
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. dissolutionThe crude product was dissolved in acetone
  7. addition37% aqueous hydrochloric acid (0.2 mL) was added
  8. filtrationThe precipitate was filtered off
  9. filtrationThe product was filtered off
  10. washwashed with water
  11. customdried
  12. customcrystallized from toluene

Sources & evidence

ORD record
ord-5e9cf6749a304b3fa987d3e605d48d1a
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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