5-Fluoro-1-indanone → HCID 58403403, compound

HRID 1897547Notes

Reaction equation

HRID 1897547 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9]N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15]2>C(O)C.C(O)(=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17]1[NH:9][C:4]3[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=3[C:16]=1[CH2:15]2

Participants

5

Reactant 2

HCID 1365375-Fluoro-1-indanoneHCID 1810602(3,5-dimethylphenyl)hydrazine

Product 1

HCID 58403403HCID 58403403, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3,5-dimethylphenylhydrazine (2.54 g, 14.7 mmol) and 5-fluoro-1-indanone (2.21 g, 14.7 mmol) in ethanol (24 mL) was added glacial acetic acid (3 drops). The solution was stirred at reflux (85° C.) for 15 minutes and cooled to room temperature. Ethanol was removed in vacuo and the resulting orange solid was dissolved in isopropanol (24 mL). Sulfuric acid (36N, 1.65 mL) was added via syringe and the mixture was stirred at reflux (90° C.) for 17 hours and subsequently cooled to room temperature. The solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass) resulting in the formation of a precipitate. The solid was collected by vacuum filtration to yield 47b in 76% crude yield (2.80 g, 11.2 mmol). Crude product was brought on to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.32-7.35 (dd, 1H, J=8.2, 5.2 Hz), 0.24-7.26 (m, 1H), 7.01-7.05 (m, 2H), 6.79 (s, 1H), 3.83 (s, 2H), 2.60 (s, 3H), 2.44 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 160.7 (d, J=361.5), 150.0 (d, J=12.0 Hz), 140.9, 140.6, 131.8, 131.2, 128.9, 122.6, 122.3, 121.6 (d, J=4.5 Hz), 117.2 (d, J=13.5 Hz), 113.4 (d, J=25.5 Hz), 113.1 (d, J=25.5 Hz), 109.6, 31.7 (d, J=3.0 Hz), 21.8, 19.3; 19F NMR (CD3CD, 376 MHz): δ −117.9 (m).

Workup

  1. temperaturecooled to room temperature
  2. customEthanol was removed in vacuo
  3. dissolutionthe resulting orange solid was dissolved in isopropanol (24 mL)
  4. additionSulfuric acid (36N, 1.65 mL) was added via syringe
  5. stirringthe mixture was stirred
  6. temperatureat reflux (90° C.) for 17 hours
  7. temperaturesubsequently cooled to room temperature
  8. additionThe solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass)
  9. customresulting in the formation of a precipitate
  10. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-83b004de5b24402fb13abc37cc333ece
Source dataset
uspto-grants-2013_08
Patent number
US08519122B2

Reaction notes

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