Hydrochloric Acid → HCID 57542291, compound

HRID 2080279Notes

Reaction equation

HRID 2080279 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[C:14]([C:19]#[N:20])=[N:15][CH:16]=[CH:17][CH:18]=1.Cl>[Pd].CO>[NH2:20][CH2:19][C:14]1[C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22939610HCID 22939610, compound

Product 1

HCID 57542291HCID 57542291, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 3-((1,3-dioxoisoindolin-2-yl)methyl)picolinonitrile (10 g, 38 mmol) and methanol (80 mL) was added conc. HCl (6.5 mL, 76 mmol) and 10% Pd/C (1 g). The mixture was stirred vigorously under 50 Psi H2 for 6 hrs. The mixture was filtered through the Celite pad and washed with methanol. The combined filtrate was concentrated to give the 2-((2-(aminomethyl)pyridin-3-yl)methyl)isoindoline-1,3-dione as a white solid in quantitative yield. LRMS (M+H+) m/z 268.1.

Workup

  1. filtrationThe mixture was filtered through the Celite pad
  2. washwashed with methanol
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-e8a4d555e1a245ccb4a349ef620521dd
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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