Hydrazine → HCID 18617216, compound

HRID 1263563Notes

Reaction equation

HRID 1263563 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=1.NN>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 18617217HCID 18617217, compound

Product 1

HCID 18617216HCID 18617216, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl 4-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]benzoate (33.2 g) in ethanol (600 mL) was added hydrazine (16.9 g). The reaction was heated to reflux and stirred for 2 h. The reaction was then cooled to r.t. and filtered. The solids were washed with ethanol (4×200 mL). The combined organic extracts were concentrated and then dissolved in CH2Cl2 and insoluble material removed by filtration. The organic extracts were concentrated to afford 17.1 g of tert-butyl 4-(4-aminobutyl)benzoate: 1H NMR (CDCl3, 400 MHz) 7.90 (d, 2H, J=8.2 Hz), 7.2 (d, 2H, J=8.0 Hz), 2.7 (m, 2H,), 1.7 (m, 4H), 1.60 (s, 9H), 1.4 (m, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe solids were washed with ethanol (4×200 mL)
  5. concentrationThe combined organic extracts were concentrated
  6. dissolutiondissolved in CH2Cl2
  7. custominsoluble material removed by filtration
  8. concentrationThe organic extracts were concentrated

Sources & evidence

ORD record
ord-7309ffbdc311487fbff450c3d918e2b6
Source dataset
uspto-grants-2003_04
Patent number
US06541492B1

Reaction notes

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