Acetic Anhydride → 1-(5-Methoxyindolin-1-yl)ethanone

HRID 1014249Notes

Reaction equation

HRID 1014249 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)(=O)C>[C:12]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 126260911-(5-Methoxyindolin-1-yl)ethanoneYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution 5-(methyloxy)-2,3-dihydro-1H-indole (8.9 g, 59.8 mmol, 1.0 eq) in acetic acid (120 mL) was added dropwise acetic anhydride (6.1 g, 59.8 mmol, 1.0 eq). The mixture was heated at 60° C. for 15 minutes. The reaction was quenched by pouring into water (100 mL). After cooling, a grey precipitate was formed, the precipitate was filtered by a Buchner funnel and rinsed with water to afford 1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indole (10.5 g, 91% yield). 1H-NMR (CDCl3, 300 MHz) δ 8.13 (d, J=6.3 Hz, 1 H), 6.74-6.71 (m, 2 H), 4.05 (t, 2 H), 3.78 (s, 3 H), 3.17 (t, 2H), 2.21 (s, 3 H).

Workup

  1. customThe reaction was quenched
  2. additionby pouring into water (100 mL)
  3. temperatureAfter cooling
  4. customa grey precipitate was formed
  5. filtrationthe precipitate was filtered by a Buchner funnel
  6. washrinsed with water

Sources & evidence

ORD record
ord-6fad4e891c774885a2f4886fb7a0ed28
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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