Acetic Anhydride → 1-(6-Nitroindolin-1-yl)ethanone

HRID 1275006Notes

Reaction equation

HRID 1275006 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13](OC(=O)C)(=[O:15])[CH3:14]>ClCCl>[C:13]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 297576-Nitroindoline

Product 1

HCID 2585661-(6-Nitroindolin-1-yl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2,3-dihydro-6-nitro-1H-indole (100 g, 0.61 mole) in dichloromethane (1000 ml) at room temperature was treated dropwise over 20 minutes with acetic anhydride (62 ml, 0.66 mole). The reaction mixture was stirred for a further 2 h, then washed with 10% Na2CO3 solution (300 ml) dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (125 g, 100%).

Workup

  1. washwashed with 10% Na2CO3 solution (300 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5987b9839db74d35b5c034fe78bbecdb
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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