Potassium Hydroxide → HCID 54098323, compound

HRID 1266436Notes

Reaction equation

HRID 1266436 reaction equation
CC1[N:3]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:13](=[O:14])[O:12][CH:11]3[CH:18]=[CH:19][CH3:20])C(C)=CC=1.Cl.NO.[OH-].[K+]>C(O)C.O>[NH2:3][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:13](=[O:14])[O:12][CH:11]2[CH:18]=[CH:19][CH3:20]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 53662592HCID 53662592, compound

Product 1

HCID 54098323HCID 54098323, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

1.1 g of 5-(2,5-dimethylpyrrol-1-yl)-3-(1-propenyl)-phthalide, 8.56 g of hydroxylamine-hydrochloride and 4.58 g of potassium hydroxide in 75 ml of ethanol/water (16:6,8, vv) are heated for 24 hours at 120° C. The solvent is distilled off, the residue is mixed with water and extracted with ethyl acetate. The ethyl acetate phase is dried (Na2SO4) and concentrated by evaporation and chromatographed on silica gel. 640 mg of 5-amino-3-(1-propenyl)-phthalide, melting point 125-130° C., is obtained with dichloromethane/methanol (99:1).

Workup

  1. distillationThe solvent is distilled off
  2. additionthe residue is mixed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase is dried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-eb89375ea8d243d399bd7cd5b55cb83c
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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