Veratroyl chloride → HCID 23369796, compound

HRID 1900756Notes

Reaction equation

HRID 1900756 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[O:13][C:5]2=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29]>N1C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28]([N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH:14]2[O:13][C:5]3=[C:6]4[C:11](=[C:2]([CH3:1])[CH:3]=[C:4]3[CH2:15]2)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]4)[CH2:18][CH2:19]1)=[O:29]

Participants

4

Reactant 2

HCID 77070Veratroyl chlorideHCID 22079784HCID 22079784, compound

Product 1

HCID 23369796HCID 23369796, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 5-methyl-2-(1-piperazinomethyl)-2,3,6,7,8,9-hexahydrofuro-[2,3-f]quinoline-7-one (1.474 g) in pyridine (40 ml), a solution of 3,4-dimethoxybenzoyl chloride (1.003 g) in pyridine (20 ml) was added dropwise while cooling on ice. Subsequently, stirring was continued at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was combined with water, and extracted with chloroform. The extract was washed with sodium bicarbonate water and water in this order, and dried and concentrated. The residue was crystallized from chloroform--n-hexane to obtain 2.163 g of a free base of the title compound as colorless prisms (mp. 190°-191° C.).

Workup

  1. temperaturewhile cooling on ice
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionextracted with chloroform
  4. washThe extract was washed with sodium bicarbonate water and water in this order
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from chloroform

Sources & evidence

ORD record
ord-41dd81e30e0b4e1497c4804ecd3e7e7a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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