Water → 1,7-Diacetyl-4-methoxyindoline

HRID 1884405Notes

Reaction equation

HRID 1884405 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15](Cl)(=[O:17])[CH3:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClCCCl.CCOCC.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[C:15](=[O:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 235059691-Acetyl-4-methoxyindoline

Product 1

HCID 232464691,7-Diacetyl-4-methoxyindolineYield 54%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-acetyl-4-methoxyindoline (4.02 g, 21 mmol) in dry 1,2-dichloroethane (30 ml) cooled in ice was added acetyl chloride (2.1 ml, 30 mmol). Powdered anhydrous AlCl3 (8.4 g, 63 mmol) was added portionwise with stirring. The mixture was stirred at rt overnight, then warmed to 50° C. for 2 h. The red/brown slurry was poured into acidified cold water (200 ml) and extracted with CH2Cl2. The combined organic phases were washed with 0.5 M aq. NaOH and brine, dried and evaporated to give a brown oil. Flash chromatography (EtOAc) followed by trituration with Et2O afforded 22 as pale yellow needles (2.22 g, 54%), mp 88-89° C., (Found: C, 66.89; H, 6.50; N, 5.95. C13H15NO3 requires C, 66.94; H, 6.48; N, 6.00%); δH (90 MHz) 7.33 (1 H, d, J 8.3, H-5), 6.61 (1 H, d, H-6), 4.17 (2 H, t, J 8.1, H-2), 3.85 (3 H, s, OMe), 3.05 (2 H, t, 3-H), 2.44 (3 H, s, 7-Ac) and 2.21 (3 H, s, N-Ac).

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. additionThe red/brown slurry was poured
  3. extractionextracted with CH2Cl2
  4. washThe combined organic phases were washed with 0.5 M aq. NaOH and brine
  5. customdried
  6. customevaporated
  7. customto give a brown oil

Sources & evidence

ORD record
ord-15423bcfc264408f91a5252ab45575f7
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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