Nitric Acid → 1-(5-Methoxy-6-nitroindolin-1-yl)ethanone

HRID 1014250Notes

Reaction equation

HRID 1014250 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.[N+:12]([O-:15])(O)=[O:13].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:15])=[O:13])[CH:10]=2)[CH2:6][CH2:7]1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 594416551-(5-Methoxy-6-nitroindolin-1-yl)ethanoneYield 62%

Procedure

To a solution of 5-(methyloxy)-2,3-dihydro-1H-indole (10.4 g, 54.4 mmol, 1.0 eq) in acetic anhydride (150 mL) was added dropwise fuming nitric acid (3.43 g, 54.4 mmol, 1.0 eq) at 0° C., then the mixture was stirred for 1 hour at r. t. After stirring for 1 hour the yellow precipitate which formed was filtered via Buchner funnel and washed with water and dried in vacuo to give 1-acetyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a yellow solid (8.0 g, 62% yield). 1H-NMR (CDCl3, 300 MHz) δ 8.43 (s, 1H), 7.31 (s, 1H), 4.13 (t, 2H), 3.87 (s, 3H), 3.22 (t, 2H), 2.14 (s, 3H).

Workup

  1. stirringAfter stirring for 1 hour the yellow precipitate which
  2. customformed
  3. filtrationwas filtered via Buchner funnel
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4771caf041af4eeabcee52c133327aee
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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