Hydrazine hydrate (1:1) → tert-butyl 1-(2-aminoethyl)-1H-pyrrole-3-carboxylate

HRID 450769Notes

Reaction equation

HRID 450769 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:15]1.O.NN>C(O)C>[NH2:3][CH2:12][CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:15]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59478522tert-butyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1H-pyrrole-3-carboxylate

Product 1

HCID 59479135tert-butyl 1-(2-aminoethyl)-1H-pyrrole-3-carboxylateYield 105.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 660 mg of tert-butyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1H-pyrrole-3-carboxylate, 194 mg of hydrazine monohydrate, and 19 ml of ethanol was stirred at 70° C. for 12 hours. The reaction solution was left to be cooled and the insoluble material was then separated by filtration. The filtrate was concentrated under reduced pressure to obtain 430 mg of tert-butyl 1-(2-aminoethyl)-1H-pyrrole-3-carboxylate as a yellow oily substance.

Workup

  1. waitThe reaction solution was left
  2. temperatureto be cooled
  3. customthe insoluble material was then separated by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7bf28f2334514824b918bf06c185bf08
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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