Acetic Anhydride → HCID 22238070, compound

HRID 1743389Notes

Reaction equation

HRID 1743389 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][C:9]1[C:17]([CH3:18])=[C:16]2[C:12]([CH2:13][CH2:14][NH:15]2)=[CH:11][C:10]=1[OH:19]>C(O)=O>[OH:19][C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([CH3:18])[C:9]=1[CH3:8])[N:15]([CH:1]=[O:3])[CH2:14][CH2:13]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22238082HCID 22238082, compound

Product 1

HCID 22238070HCID 22238070, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To formic acid (100 mL) was added acetic anhydride (23 mL, 0.24 mol) under ice-cooling, and the mixture was stirred at room temperature for 40 minutes. To this solution was added 2,3-dihydro-6,7-dimethyl-1H-indole-5-ol (20.0 g, 0.12 mol) under ice-cooling, and the mixture was stirred at room temperature for 75 minutes. The reaction mixture was concentrated under reduced pressure, and dissolved in the mixture of chloroform-methanol. To this was added an aqueous solution of sodium bicarbonate solution to neutralize, the organic layer was separated, and the aqueous layer was extracted with chloroform three times. The combined organic layers were washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The solid was washed with diisopropyl ether to obtain 22.0 g of the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 75 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutiondissolved in the mixture of chloroform-methanol
  6. additionTo this was added an aqueous solution of sodium bicarbonate solution
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform three times
  9. washThe combined organic layers were washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. washThe solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-1efbfc2b6a7745fca567dc4343e6b0af
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

Loading…