HCID 59226503, compound → 2-(3-(3-Aminopyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione

HRID 2046773Notes

Reaction equation

HRID 2046773 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:11]=1)([O-])=O>CC(O)=O.[Fe]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH:11]=1

Participants

4

Reactant 1

HCID 59226503HCID 59226503, compound

Product 1

HCID 592265372-(3-(3-Aminopyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dioneYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1.0 equiv.) in AcOH (0.38 M) was added Fe (6.0 equiv.) and the reaction was stirred at room temperature for 2 h. Filtered, then washed with methanol and concentrated the filtrate. To the crude was added ethyl acetate and saturated NaHCO3, the organics were dried with Na2SO4, and concentrated to give 2-(3-(3-aminopyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione as a yellow thick gum in 96% yield. LC/MS=320.0 (M+H), LC=2.410 min.

Workup

  1. filtrationFiltered
  2. washwashed with methanol
  3. concentrationconcentrated the filtrate
  4. additionTo the crude was added ethyl acetate and saturated NaHCO3
  5. dry with materialthe organics were dried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9391de791d194d0382970e7161bbc42a
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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