tert-Butyl methyl ether → 5-Amino-2,3-dihydro-isoindol-1-one

HRID 2362257Notes

Reaction equation

HRID 2362257 reaction equation
[NH4+].[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.COC(C)(C)C>C(O)C.O.C(O)C.[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 3

HCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 140056255-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 219562395-Amino-2,3-dihydro-isoindol-1-oneYield 48.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of Fe (1.1 g, 19.6 mmole), NH4Cl (1.5 g, 28 mmole) in a mixture of ethanol/water (30 ml/7 ml) at 80° C. was added a mixture of 5-Nitro-2,3-dihydro-isoindol-1-one (1 g, 5.6 mmole) in 10 ml ethanol. The reaction mixture was stirred at 80° C. for 2 hours. Mixture was cooled down, filtered off, solid was washed with 50 ml ethanol. The filtrate was concentrated, taken into 50 ml ethylacetate, washed with 20 ml water. Organic layer was dried over Na2SO4, filtered and concentrated to give about 900 mg crude. Trituration with methyl t-butylether gave 400 mg pure product, 48% yield.

Workup

  1. additionwas added
  2. temperatureMixture was cooled down
  3. filtrationfiltered off
  4. washsolid was washed with 50 ml ethanol
  5. concentrationThe filtrate was concentrated
  6. washwashed with 20 ml water
  7. dry with materialOrganic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give about 900 mg crude

Sources & evidence

ORD record
ord-d4f7a5121852462585b29b488e150869
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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