1-Indanone → HCID 67352385, compound

HRID 2369224Notes

Reaction equation

HRID 2369224 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10]N)[CH:7]=[CH:8][CH:9]=1.[C:12]1(=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>C(O)C.C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]2[C:13]3[CH2:12][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]=3[NH:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 67351-IndanoneHCID 27239403-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 67352385HCID 67352385, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-methoxyphenylhydrazine hydrochloride (3.65 g, 20.9 mmol) and 1-indanone (2.77 g, 21.0 mmol) in ethanol (11.8 mL) was added glacial acetic acid (3 drops). The solution was stirred at reflux (85° C.) for 15 minutes and cooled to room temperature. Orange precipitate began to form upon cooling, and the mixture was subsequently emerged in an ice water bath to further induce crystallization. The solid was collected by vacuum filtration and dissolved in 22 mL isopropanol. Sulfuric acid (36 N, 1.5 mL) was added via syringe, and the resulting solution was stirred at reflux (90° C.) for 16 hours. Upon cooling to room temperature, the solution was basified to pH 10 with aqueous sodium hydroxide (2% by mass) resulting in the formation of precipitate. The solid was collected by vacuum filtration to yield 29a as an orange solid (2.55 g, 10.9 mmol). Crude product was brought on to the next step without purification. For purposes of characterization, the product was purified by flash column chromatography (20:1 hexanes—ethyl acetate). 1H NMR (600 MHz, CDCl3): δ 8.18 (s, 1H), 7.50-7.52 (m, 2H), 7.40-7.41 (d, 1H, J=7.2 Hz), 7.30-7.32 (t, 1H, J=7.8 Hz), 7.16-7.19 (td, 1H, J=7.8, 1.2 Hz), 6.95 (d, 1H, J=2.4 Hz), 6.83-6.84 (dd, 1H, J=8.4, 2.4 Hz), 3.88 (s, 3H), 3.69 (s, 2H); 13C NMR (150 MHz, CDCl3): δ 156.2, 147.3, 142.3, 141.5, 135.3, 126.5, 125.3, 124.1, 121.9, 119.5, 119.4, 116.7, 109.6, 96.2, 55.7, 30.3. FTIR: cm−1 3399, 1612, 1405, 1255, 1155, 1041, 820. ESI-HRMS: Calcd. for C16H13NO+ [M]+: 235.0992. found 235.0990.

Workup

  1. temperaturecooled to room temperature
  2. customto form
  3. temperatureupon cooling
  4. customthe mixture was subsequently emerged in an ice water bath to further induce crystallization
  5. filtrationThe solid was collected by vacuum filtration
  6. dissolutiondissolved in 22 mL isopropanol
  7. additionSulfuric acid (36 N, 1.5 mL) was added via syringe
  8. stirringthe resulting solution was stirred
  9. temperatureat reflux (90° C.) for 16 hours
  10. temperatureUpon cooling to room temperature
  11. customresulting in the formation of precipitate
  12. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-738a9e7c867c449d96d57bf4ff52d155
Source dataset
uspto-grants-2014_04
Patent number
US08703936B2

Reaction notes

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