Water → HCID 23499225, compound

HRID 1836311Notes

Reaction equation

HRID 1836311 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH2:3]1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].O.C(OCC)(=O)C>N1C=CC=CC=1>[OH:17][CH2:16][C:15]([CH:4]1[CH2:3][CH:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5]1)([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 62324Propionyl chlorideHCID 234992302-(4-Amino-6-nitro-1,2,3,4-tetrahydroquinolin-2-yl)-2-methylpropan-1-ol

Product 1

HCID 23499225HCID 23499225, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound of Example 22 (50 mg) and 0.1 ml of propionyl chloride were dissolved in 1 ml of pyridine. After 2 hours of stirring at room temperature, water and ethyl acetate were added. The ethyl acetate layer was washed with water, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was dissolved in 1 ml of methanol, 0.1 ml of a 4N aqueous solution of sodium hydroxide was added, and the mixture was stirred for 1 hour. Then, a phosphate buffer (pH 7.0) was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain 31 mg of the title compound. Its physical properties are shown below.

Workup

  1. washThe ethyl acetate layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. dissolutionThe residue was dissolved in 1 ml of methanol
  5. addition0.1 ml of a 4N aqueous solution of sodium hydroxide was added
  6. stirringthe mixture was stirred for 1 hour
  7. additionThen, a phosphate buffer (pH 7.0) was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-5b371854d3704920afc06597cd5ea4d9
Source dataset
uspto-grants-2004_08
Patent number
US06777427B2

Reaction notes

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