Hydrochloric Acid → 5-Amino-2,3-dihydro-isoindol-1-one

HRID 2375869Notes

Reaction equation

HRID 2375869 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>CCO.N.CO.[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

8

Reactant 3

HCID 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 4

HCID 222AmmoniaCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

Iron powder (158 mg, 2.83 mmol), water (61 μL), and HCl (37%, 5 μL, 0.566 mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-1-one (50.4 mg, 0.283 mmol) in EtOH (754 μL). The above mixture was heated at 95° C. for 2 h. After that time, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid was filtered off. The filtrate was concentrated in vacuo to obtain a light-yellow solid that was purified by preparative TLC eluting with 10% MeOH/CH2Cl2 to give a light-yellow solid of 5-amino-2,3-dihydroisoindol-1-one. 1H NMR (CD3OD, 400 MHz): δ=7.48 (s, 1H), 8.08 (s, 2H), 9.91 (s, 1H), 10.66 (d, 1H, J=8.8 Hz). MS (ES+): m/z 149.21 (100) [MH+]. HPLC: tR=1.20 min (ZQ2000, polar—5 min).

Workup

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto obtain a light-yellow solid
  4. customthat was purified by preparative TLC
  5. washeluting with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-807d8ac634e54716a171e68cf7bc9d6d
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…