Acetic Anhydride → Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)-

HRID 1647037Notes

Reaction equation

HRID 1647037 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 362195-Nitroindoline

Product 1

HCID 36566Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-nitroindoline (I, 12.012 g) in pyridine (100 ml) and acetic anhydride (50 ml) is stirred for 17 hr under argon. The mixture is then concentrated under reduced pressure to give the title compound, mp 175°-177°; NMR (CDCl3, 300 MHz) 8.28, 8.10, 8.01, 4.23, 3.31 and 2.28 δ; CMR (CDCl3, 75.47 MHz) 23.95, 27.01, 49.11, 115.73, 119.93, 124.27, 132.4, 143.4 and 169.8 δ; IR (CHCl3) 1680, 1600, 1480, 1470, 1390, 1340 and 1320 cm-1.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure

Sources & evidence

ORD record
ord-361a2566a11345ae9440cb335160eaa3
Source dataset
uspto-grants-1993_01
Patent number
US05182403

Reaction notes

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