Water → HCID 15917430, compound

HRID 648092Notes

Reaction equation

HRID 648092 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8](C)[CH2:7][C:6]12[CH2:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16]1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:7][C:6]12[CH2:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15917428HCID 15917428, compound

Product 1

HCID 15917430HCID 15917430, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6',7'-dimethoxy-2'-methylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (20.6 g), ethyl chloroformate (10.9 g) and potassium carbonate (20 g) in dry benzene (400 ml) is heated under reflux overnight. The reaction mixture is cooled and stirred with water (200 ml) for 15 minutes. The organic phase is washed with water, diluted hydrochloric acid, saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield 14.9 g of product as an oil. An analytical sample is obtained by passing 2.0 g of the oil through a silical gel dry column using ethyl acetate as the eluent and chloroform as the extractor. Removal of the solvent yields 1.8 g of an oil which crystallizes in the cold over petroleum ether, yielding a solid, mp, 72°-76°. The solid is recrystallized from hexane to yield white crystals, mp 75°-76°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction mixture is cooled
  4. washThe organic phase is washed with water, diluted hydrochloric acid, saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-41a2ebb8ea1248138dae7676b35d13d8
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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