Ethanol → HCID 59314231, compound

HRID 1047683Notes

Reaction equation

HRID 1047683 reaction equation
C[O:2][C:3]([C:5]1([NH:18][C:19](=[O:31])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=2[O:27][CH:28](C)[CH3:29])[CH2:16][C:15]2[C:17]3[C:11]([CH:12]=[CH:13][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:6]1)=[O:4].[OH-].[K+].O.[CH3:35]CO>>[CH2:28]([O:27][C:21]1[C:22]([CH3:26])=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][C:5]1([C:3]([OH:2])=[O:4])[CH2:16][C:15]2[C:17]3[C:11]([CH:12]=[CH:13][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:6]1)=[O:31])[CH:29]=[CH2:35]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 59314329HCID 59314329, compound

Product 1

HCID 59314231HCID 59314231, compoundYield 93%

Procedure

The mixture of 2-(2-isopropoxy-3-methyl-benzoylamino)-2,3-dihydro-1H-phenalene-2-carboxylic acid methyl ester (25) (143 mg, 0.34 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 of the water. The precipitate is filtered to give a pure product (26) as white solid (127 mg, 93%).

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-16047c7d4d9d4a668f5dec26c4da896c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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