Water → HCID 18941413, compound

HRID 356219Notes

Reaction equation

HRID 356219 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:18])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:21]I.O>O1CCCC1.C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2([CH3:21])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18941448HCID 18941448, compound

Product 1

HCID 18941413HCID 18941413, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-[(3-Aminophenyl)methyl]indan-1-one (5.18 g, 22.0 mmol) in tetrahydrofuran (100 mL) was slowly added to a suspension of sodium hydride (2.20 g, 65.0 mmol), and tetrahydrofuran (100 mL) at room temperature and the mixture was stirred for 30 min. Methyl iodide (1.63 mL, 26.0 mmol) was added and the resulting mixture was stirred at room temperature for 5 h. Water (150 mL) was added, followed by methylene chloride (150 mL) and the resulting aqueous layer was washed with several portions of methylene chloride. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a solid: mp 95°-98° C., MS MH+252.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 5 h
  2. washthe resulting aqueous layer was washed with several portions of methylene chloride
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-274fc886381d4c6f9c3aa7833c760825
Source dataset
uspto-grants-1998_11
Patent number
US05834521

Reaction notes

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