1-Propanol → HCID 15917432, compound

HRID 1758520Notes

Reaction equation

HRID 1758520 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:15]([O:17]CC)=[O:16])[CH2:7][C:6]12[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20]1.[OH-:28].[K+].[CH2:30]([OH:33])[CH2:31][CH3:32]>O>[C:15]([OH:17])(=[O:16])/[CH:32]=[CH:31]\[C:30]([OH:28])=[O:33].[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][NH:8][CH2:7][C:6]12[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20]1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 14797Potassium HydroxideHCID 15917430HCID 15917430, compound

Product 1

HCID 15917432HCID 15917432, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6',7'-dimethoxy-2'-ethoxycarbonylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (4.2 g), potassium hydroxide (7.0 g) and water (7.0 ml) in n-propanol (150 ml) is heated under reflux for four hours. Removal of the solvent under reduced pressure yields an oil which is stirred in water (300 ml) and then extracted with chloroform. The combined organic phases are washed with water, saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield 3.1 g (81%) of product as an oil which is dissolved in ether and converted to the maleate salt (1.9 g), mp 165°-167°. The material is twice recrystallized from ethyl acetate/methanol to yield a white solid (1.4 g), mp 180°-181° (dec.)

Workup

  1. temperatureis heated
  2. temperatureunder reflux for four hours
  3. customRemoval of the solvent under reduced pressure
  4. customyields an oil which
  5. extractionextracted with chloroform
  6. washThe combined organic phases are washed with water, saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customthe solvent is removed

Sources & evidence

ORD record
ord-64ae69cba05749c684b18b7b736521f4
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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