HCID 10810402, compound → HCID 10831411, compound

HRID 613647Notes

Reaction equation

HRID 613647 reaction equation
[Cl:1][C:2]1[C:20]([CH:21]2OCC[O:22]2)=[CH:19][CH:18]=[C:17]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2>C(O)(=O)C>[Cl:1][C:2]1[C:20]([CH:21]=[O:22])=[CH:19][CH:18]=[C:17]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

3

Reactant 1

HCID 10810402HCID 10810402, compound

Product 1

HCID 10831411HCID 10831411, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8-[2,6-dichloro-3-(1,3-dioxolan-2-yl)benzyloxy]-2-methylquinoline (3.0 g) in 80% acetic acid (30 ml) was heated at 60° C. for 2 hours. The cooled reaction mixture was concentrated in vacuo, and aqueous sodium bicarbonate solution was added thereto. The mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate to give 8-(2,6-dichloro-3-formylbenzyloxy)-2-methylquinoline (2.28 g) as colorless crystals.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo, and aqueous sodium bicarbonate solution
  3. additionwas added
  4. extractionThe mixture was extracted with chloroform
  5. washthe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-0eb62446c7f2491088da24803e4f5556
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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