Isopropanol → HCID 14747776, compound

HRID 1609506Notes

Reaction equation

HRID 1609506 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-92bb9d14f3d448a9897ef7325b5fe841
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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