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

HRID 1014244Notes

Reaction equation

HRID 1014244 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[C:10]([N+:22]([O-:24])=[O:23])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 126260911-(5-Methoxyindolin-1-yl)ethanone

Product 1

HCID 594416551-(5-Methoxy-6-nitroindolin-1-yl)ethanoneYield 65%

Conditions

Temperature
0 °C

Procedure

A 4-neck 22 L round bottom flask equipped with mechanical stirrer and thermowell was charged with 1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indole (300 g, 1.56 mol) made in accordance with Step B, immediately above, and acetic anhydride (12 L). The resulting mixture was cooled to 0° C. then nitric acid (70%,.100 mL, 1.56 mol) was added dropwise. The reaction was stirred at room temperature overnight and then cooled to 0° C. The solid formed was collected by vacuum filtration and washed with water (200 mL) and MTBE (200 mL), then dried in a oven to give 1-acetyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a yellow solid (239 g, 65% 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. customA 4-neck 22 L round bottom flask equipped with mechanical stirrer
  2. temperaturecooled to 0° C
  3. customThe solid formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water (200 mL) and MTBE (200 mL)
  6. customdried in a oven

Sources & evidence

ORD record
ord-01885880eea640a38bda2f6aeb5f3609
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…