Phosphoric Acid → 2-Nitro-5-(2-quinolylmethoxy)benzaldehyde

HRID 1721685Notes

Reaction equation

HRID 1721685 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.P(=O)(O)(O)O.C(OCC)(=O)C>CS(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 106148772-Nitro-5-(2-quinolylmethoxy)benzyl alcohol

Product 1

HCID 106625692-Nitro-5-(2-quinolylmethoxy)benzaldehydeYield 72.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 2-nitro-5-(2-quinolylmethoxy)benzyl alcohol (1.74 g, 5.6 mmol), prepared in step 1, and dicyclohexylcarbodiimide (3.71 g, 18 mmol) in DMSO (25 ml) was added 1M solution of phosphoric acid in DMSO (2.7 ml), and the resulting mixture was stirred at room temperature for 1 hour. Ethyl acetate (100 ml) was then added and the precipitated dicyclohexylurea was filtered off. The filtrate was washed with water, and brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (silica gel, methylene chloride-ethyl acetate 15:1) to afford 1.25 g of 2-nitro-5-(2-quinolylmethoxy)benzaldehyde.

Workup

  1. filtrationthe precipitated dicyclohexylurea was filtered off
  2. washThe filtrate was washed with water, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, methylene chloride-ethyl acetate 15:1)

Sources & evidence

ORD record
ord-9ca48c6dfb4044a6b8a1ee16bb2a89ca
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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