Ammonium → 5-nitro-2,3-dihydro-1H-isoindol-1-one

HRID 1487208Notes

Reaction equation

HRID 1487208 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[NH4+:16]>>[N+:13]([C:11]1[CH:12]=[C:3]2[C:4](=[CH:9][CH:10]=1)[C:5](=[O:6])[NH:16][CH2:2]2)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 223AmmoniumHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 140056255-nitro-2,3-dihydro-1H-isoindol-1-one

Procedure

A suspension of methyl 2-(bromomethyl)-4-nitrobenzoate in ammonium solution (7 N in methanol, 5 mL) was stirred at room temperature for 2 hours and concentrated in vacuum to obtain a yellow solid. This crude solid was triturated with ethyl acetate (15 mL) and was then cooled at −20° C. The mixture was filtered to obtain the product 5-nitroisoindolin-1-one as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.04 (br s, 1H), 8.48 (d, 1H, J=2.0 Hz), 8.25 (dd, 1H, J=2.0 Hz, 8.4 Hz), 7.91 (d, 1H, J=8.4 Hz), 4.51 (s, 2H).

Workup

  1. concentrationconcentrated in vacuum
  2. customto obtain a yellow solid
  3. customThis crude solid was triturated with ethyl acetate (15 mL)
  4. temperaturewas then cooled at −20° C
  5. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-6773d9facd29471e9f64cfb40b796c3d
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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