Methanol → HCID 22247299, compound

HRID 1107982Notes

Reaction equation

HRID 1107982 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([OH:24])=[O:23])=[C:15]([CH3:21])[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].S(=O)(=O)(O)O.[CH3:30]O>>[CH2:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([O:24][CH3:30])=[O:23])=[C:15]([CH3:21])[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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22247310HCID 22247310, compound

Product 1

HCID 22247299HCID 22247299, compound

Procedure

1-Octyl-5-carboxy-6-methyl-7-nitroindoline (1.4 g) was dissolved in methanol (30 ml), and conc. sulfuric acid (4.1 g) was added, which was followed by refluxing for 4 hr. Methanol was evaporated under reduced pressure. 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: chloroform/methanol=1/0-10/1) to give 750 mg of 1-octyl-5-methoxycarbonyl-6-methyl-7-nitroindoline as crystals.

Workup

  1. temperatureby refluxing for 4 hr
  2. customMethanol was evaporated under reduced pressure
  3. additionEthyl acetate (100 ml) was 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: chloroform/methanol=1/0-10/1)

Sources & evidence

ORD record
ord-1ae093df753d47929077fc6e22dee36b
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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