Water → HCID 15917442, compound

HRID 1758522Notes

Reaction equation

HRID 1758522 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH2:6][C:7]3([O:26][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][N:9](C(OC1C=CC=CC=1)=O)[CH2:8]3.[OH-].[K+].O>C(O)CC>[ClH:1].[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH2:6][C:7]3([O:26][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][NH:9][CH2:8]3

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 15917440HCID 15917440, compound

Product 1

HCID 15917442HCID 15917442, compoundYield 137.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 6-chloro-2'-phenoxycarbonylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (25.0 g), potassium hydroxide (25 g) and water (25 ml) in n-propanol (250 ml) is heated under reflux for four hours. Removal of the solvent under reduced pressure yields a solid which is stirred with water (500 ml) and extracted with ether. The combined ether extract is washed with 3 N hydrochloric acid and basified with saturated sodium carbonate solution. The material which separates is extracted with ether, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield product as a solid (13.5 g, 78%). A 4.0 g-portion of the solid is dissolved in ether and converted to the product hydrochloride salt (4.3 g). An analytical sample is twice recrystallized from ethyl acetate/methanol, mp 238°-239° (dec).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for four hours
  3. customRemoval of the solvent under reduced pressure
  4. customyields a solid which
  5. extractionextracted with ether
  6. extractionThe combined ether extract
  7. washis washed with 3 N hydrochloric acid and basified with saturated sodium carbonate solution
  8. extractionThe material which separates is extracted with ether
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationAfter filtering
  12. customthe solvent is removed

Sources & evidence

ORD record
ord-0d59ca71d3fe4dc984b97facd5c19be7
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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