Sulfuric Acid → 4,7-Dimethyl-5-[2-(morpholin-4-yl)ethoxy]-1H-indole-2,3-dione

HRID 1822902Notes

Reaction equation

HRID 1822902 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:10]([CH3:22])=[CH:9][C:8]=1[NH:23][C:24](=[O:28])[CH:25]=NO.C([O-])(O)=[O:30].[Na+]>>[CH3:22][C:10]1[C:11]([O:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[CH:12][C:7]([CH3:6])=[C:8]2[C:9]=1[C:25](=[O:30])[C:24](=[O:28])[NH:23]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 73867562HCID 73867562, compound

Product 1

HCID 221696924,7-Dimethyl-5-[2-(morpholin-4-yl)ethoxy]-1H-indole-2,3-dioneYield 87%

Conditions

Temperature
75 °C

Procedure

To concentrated H2SO4 (3.5 mL) at 60° C. was added N-[2,5-dimethyl-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-hydroxyimino-acetamide (1.4 g, 4.36 mmol) in portions with stirring. After the addition was finished, the mixture was heated to 75° C. and kept at this temperature for 15 min. A dark-purple solution was formed and poured upon cracked ice. Then solid NaHCO3 is added and pH was adjusted to 8.0. The mixture was extracted with CH2Cl2, dried (Na2SO4), and crystallized from CH2Cl2-hexane to give 4,7-Dimethyl-5-(2-morpholin-4-yl-ethoxy)-1H-indole-2,3-dione as brown solid 1.15 g, 87%).

Workup

  1. additionAfter the addition
  2. customA dark-purple solution was formed
  3. additionpoured
  4. extractionThe mixture was extracted with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. customcrystallized from CH2Cl2-hexane

Sources & evidence

ORD record
ord-e423bf5b074645c39a9f2898bb73a1bf
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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