Hydrazine → HCID 22287002, compound

HRID 1837620Notes

Reaction equation

HRID 1837620 reaction equation
NN.C1(=O)[N:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:19][CH:18]3[CH:13]([CH2:14][C:15]4[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=4[CH2:17]3)[CH2:12]2)C(=O)C2=CC=CC=C12>C(O)C>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:19][CH:18]2[CH:13]([CH2:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[CH2:17]2)[CH2:12]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22287001HCID 22287001, compound

Product 1

HCID 22287002HCID 22287002, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (42 mg, 1.31 mmol) was added to a solution of 2-(3-Phthalimido-n-prop-1-yl)-2,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole (200 mg, 0.65 mmol) in 5 mL of ethanol, and the mixture was refluxed for 20 hours, over which time a white solid had precipitated. The mixture was cooled to room temperature, the solid was removed by filtration, and the filtrate was concentrated in-vacuo. The residue was suspended in chloroform, and the solids were removed by filtration. The filtrate was concentrated in-vacuo to 90 mg of a yellow oil as product. NMR (300 MHz, CDCl3) δ7.16-7.08 (m, 4H), 3.39-3.32 (m, 2H), 3.04-2.98 (m, 6H), 2.80-2.61 (m, 4H), 2.08-2.05 (m, 2H), 1.90-1.79 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed for 20 hours, over which time a white solid
  2. customhad precipitated
  3. customthe solid was removed by filtration
  4. concentrationthe filtrate was concentrated in-vacuo
  5. customthe solids were removed by filtration
  6. concentrationThe filtrate was concentrated in-vacuo to 90 mg of a yellow oil as product

Sources & evidence

ORD record
ord-606066119dd34484a6016b6e7a6d7dad
Source dataset
uspto-grants-2004_08
Patent number
US06784200B2

Reaction notes

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