Hydrazine → Ammonium Hydroxide

HRID 551085Notes

Reaction equation

HRID 551085 reaction equation
[O:1]=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]12[C:24](=[O:25])[NH:23][C:21]3[C:22]1=[C:17]([CH:18]=[CH:19][CH:20]=3)[NH:16][C:15](=[O:26])[CH2:14]2.NN>CCO>[NH4+:3].[OH-:1].[NH2:3][CH2:12][C:13]12[C:24](=[O:25])[NH:23][C:21]3[C:22]1=[C:17]([CH:18]=[CH:19][CH:20]=3)[NH:16][C:15](=[O:26])[CH2:14]2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 67173953(+/-)-2a-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione

Product 2

HCID 14923Ammonium HydroxideHCID 57663772(+/-)-2a-(Aminomethyl)-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-2a-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione from Step A (2.30 g, 6.62 mmol) and hydrazine (1.05 mL, 33.1 mmol) in EtOH (30 mL) was heated at 70° C. for 2 h, then cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:9:1, to give the title compound. MS: m/z=218 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-7e3ece8a3df344218241444115925d24
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…