Ammonia → 5-Amino-2,3-dihydro-isoindol-1-one

HRID 1039087Notes

Reaction equation

HRID 1039087 reaction equation
O.Cl.[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][CH2:9]2)([O-])=O.N>CCO.[Fe]>[NH2:3][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][CH2:9]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 140056255-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 219562395-Amino-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Iron powder (2.51 g, 45 mmol), water (0.97 ml) and HCl (37%, 0.74 ml), were added to a stirred suspension of the 5-nitroisoindolin-1-one (800 mg, 4.5 mmol) from step 2 of this example in EtOH (11.2 ml). The mixture was heated at 95° C. for 2 h. Ammonia (7N in MeOH) was added (1 mL) to make the pH of the mixture alkaline. The mixture was filtered to removed undissolved solids and the filter cake washed with EtOH (2×40 ml). The filtrate and organic washes were combined and concentrated in vacuum to give the titled compound.

Workup

  1. filtrationThe mixture was filtered
  2. customto removed undissolved solids
  3. washthe filter cake washed with EtOH (2×40 ml)
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-c3d19c53996c4330be95266fb33456dd
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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