Isopropanol → HCID 14747776, compound

HRID 483851Notes

Reaction equation

HRID 483851 reaction equation
[OH:1][CH:2]([CH3:30])[CH2:3][N:4]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH:16]=[CH:15]2)=[O:6].[Cr](O)(O)(=O)=O.C(O)(C)C>C(O)(=O)C>[C:2]([CH2:3][N:4]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH:16]=[CH:15]2)=[O:6])(=[O:1])[CH3:30]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24425Chromic AcidHCID 54121131HCID 54121131, compound

Product 1

HCID 14747776HCID 14747776, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 3 ml of acetic acid is dissolved 0.2 g of 6-{4-[N-(2-hydroxypropyl)-N-cyclohexylmethylaminocarbonyl]butoxy}carbostyril. Thereto is dropwise added 0.3 ml of an aqueous solution containing 0.07 g of chromic acid at room temperature. The mixture is stirred for 1 hour, and 0.3 ml of isopropyl alcohol is added. Acetic acid is removed by evaporation under reduced pressure. The residue is made alkaline with sodium bicarbonate and then extracted with chloroform. The extract is washed with water and dried with anhydrous magnesium sulfate. The solvent is removed by evaporation. The residue is purified by means of a silica gel column chromatography (eluent; chloroform:methanol=20:1) and recrystallized from diethyl ether to obtain 0.07 g of 6-[4-(N-acetylmethyl-N-cyclohexylmethylaminocarbonyl)butoxy]carbostyril.

Workup

  1. customAcetic acid is removed by evaporation under reduced pressure
  2. extractionextracted with chloroform
  3. washThe extract is washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent is removed by evaporation
  6. customThe residue is purified by means of a silica gel column chromatography (eluent; chloroform:methanol=20:1)
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-9d9e55d3209c489cb8c0137904f8e62c
Source dataset
uspto-grants-1993_07
Patent number
US05227381

Reaction notes

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