Toluene → HCID 69640155, compound

HRID 2188231Notes

Reaction equation

HRID 2188231 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=O)[C:8]3[C:13]([NH:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC=CC=1.[OH-].[Na+]>C(OCC)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:13]([NH:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 64542543-Methoxyacridin-9-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 69640155HCID 69640155, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 15.29 g of 3-methoxyacridone (67.9 mmol) in 200 mL of diethyl ether was added 7.73 g of LiAlH4 slowly portionwise. Once evolution of H2 ceased, 200 mL of dry toluene was added under inert atmosphere and the reaction was stirred at reflux for 2 h. The reaction mixture was cooled to 0° C. and dropwise addition of 8.0 mL of water, 8.0 mL of 15% NaOH (aq) and 24.0 mL of water were performed sequentially. 500 mL of CH2Cl2 was added and the resultant precipitate was filtered, washed with 500 mL of CH2Cl2 and discarded. The filtrate was concentrated in vacuo, resuspended in hexanes, and again concentrated to afford 14.06 g of 3-methoxyacridan (98%).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with 500 mL of CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. concentrationagain concentrated

Sources & evidence

ORD record
ord-a42fb745cc114cd9bd1d48021690e9cb
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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