1-Propanol → HCID 22247310, compound

HRID 1107981Notes

Reaction equation

HRID 1107981 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=C[C:14](C#N)=[C:15](C)[C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-:24].[Na+].[CH2:26]([OH:29])[CH2:27][CH3:28]>O>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:28][C:27]([C:26]([OH:24])=[O:29])=[C:15]([CH3:14])[C:16]=2[N+:18]([O-:20])=[O:19])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 22247294HCID 22247294, compound

Product 1

HCID 22247310HCID 22247310, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Octyl-5-cyano-6-methyl-7-nitroindoline (2.4 g) was dissolved in n-propanol and a solution of NaOH (3.0 g) in water (10 ml) was added, which was followed by refluxing for 20 hr. n-Propanol was evaporated under reduced pressure and ethyl acetate (100 ml) was added to the residue. The mixture was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzenel1/5-1/1) to give 1.4 g of 1-octyl-5-carboxy-6-methyl-7-nitroindoline as crystals.

Workup

  1. temperatureby refluxing for 20 hr
  2. customn-Propanol was evaporated under reduced pressure and ethyl acetate (100 ml)
  3. additionwas added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEthyl acetate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzenel1/5-1/1)

Sources & evidence

ORD record
ord-b0ffe12235104c7aa81dbf819e03f31e
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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