Methanol → HCID 14668083, compound

HRID 1974672Notes

Reaction equation

HRID 1974672 reaction equation
Cl.[NH2:2][C:3]1[C:4]([CH:32]=[O:33])=[CH:5][C:6]2[CH2:7][CH2:8][C:9]3[C:10]([CH2:28][CH2:29][CH2:30][CH3:31])=[C:11]4[CH2:20][CH2:19][CH2:18][C:17](=CC5C=CC=CC=5)[C:12]4=[N:13][C:14]=3[C:15]=2[N:16]=1.C[OH:35]>ClCCl>[NH2:2][C:3]1[C:4]([CH:32]=[O:33])=[CH:5][C:6]2[CH2:7][CH2:8][C:9]3[C:10]([CH2:28][CH2:29][CH2:30][CH3:31])=[C:11]4[CH2:20][CH2:19][CH2:18][C:17](=[O:35])[C:12]4=[N:13][C:14]=3[C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 373789HCID 373789, compound

Product 1

HCID 14668083HCID 14668083, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.46 g (1 mmol) of 2-amino-11-benzylidene-7-n-butyl-5,6,8,9,10,11-hexahydrobenzo[b][1,10]phenanthroline-3-carboxaldehyde HCl salt (XX) in 40 mL of dichloromethane and 20 mL of methanol is stirred at approximately -78° C. and ozone is bubbled through the orangish-yellow solution. When the color of the reaction mixture changes to pale greenish-yellow, the solution is immediately purged by bubbling in N2 for 5 minutes. Dimethylsulfide (1.0 mL) is added and the reaction mixture is allowed to warm to room temperature. The solvents are removed by rotary evaporation and the residue is triturated with 100 mL of ether, yielding 0.39 g (100%) of product.

Workup

  1. customozone is bubbled through the orangish-yellow solution
  2. customWhen the color of the reaction mixture changes to pale greenish-yellow, the solution is immediately purged
  3. customby bubbling in N2 for 5 minutes
  4. additionDimethylsulfide (1.0 mL) is added
  5. customThe solvents are removed by rotary evaporation
  6. customthe residue is triturated with 100 mL of ether

Sources & evidence

ORD record
ord-834ba1025304400aada29efce8e16d3e
Source dataset
uspto-grants-1994_02
Patent number
US05283333

Reaction notes

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