Water → HCID 59314231, compound

HRID 1047681Notes

Reaction equation

HRID 1047681 reaction equation
C([O:3][C:4]([C:6]1([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=2[O:28][CH2:29][CH:30]=[CH2:31])[CH2:17][C:16]2[C:18]3[C:12]([CH:13]=[CH:14][CH:15]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH2:29]([O:28][C:22]1[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:6]1([C:4]([OH:5])=[O:3])[CH2:17][C:16]2[C:18]3[C:12]([CH:13]=[CH:14][CH:15]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:7]1)=[O:32])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68590795HCID 68590795, compound

Product 1

HCID 59314231HCID 59314231, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-allyloxy-3-methyl-benzoylamino)-2,3-dihydro-1H-phenalene-2-carboxylic acid ethyl ester (23) (107 mg, 0.26 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 mL) and water (0.5 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until no more white precipitate came out from the water. The precipitate is filtered to give a pure product (24) as white solid (98 mg, 94%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-5895a810215441ef9298755c1b4de6c1
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…