Hydrochloric Acid → 2,3-Dihydro-1H-isoindol-5-amine

HRID 1931170Notes

Reaction equation

HRID 1931170 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=2)[CH2:9]1)C1C=CC=CC=1.Cl>CCO.[OH-].[OH-].[Pd+2]>[NH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:16]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 120659772-Benzyl-5-nitroisoindoline2×

Product 1

HCID 147958622,3-Dihydro-1H-isoindol-5-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Part B. To a solution of the isoindoline (5.40 g, 21.3 mmol) made above in EtOH (266 mL) under N2 was added 20% Pd(OH)2/C (3.00 g, 4.25 mmol). The reaction mixture was hydrogenated at 45 psi for 1 h. TLC analysis indicated that the nitro functionality was reduced and the Bn group was still intact. Therefore, concentrated HCl (1.6 mL, 19.1 mmol) was added to the reaction mixture and hydrogenation (50 psi) was continued overnight. The mixture was filtered through Celite®, washed with MeOH, and the filtrate was concentrated to one fourth of the volume. The precipitate was filtered off to provide the 5-aminoisoindoline.HCl (1.32 g, 36% yield): 1H NMR (500 MHz, CDCl3) δ 9.88 (s, br, 2H), 7.00 (d, 1H), 6.54 (m, 2H), 5.44 (s, br, 2H), 4.32 (s, 2H), 4.28 (s, 2H); ESI MS m/z 135 (M−HCl+H)+.

Workup

  1. waitwas continued overnight
  2. filtrationThe mixture was filtered through Celite®
  3. washwashed with MeOH
  4. concentrationthe filtrate was concentrated to one fourth of the volume
  5. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-cba36c0af5ab42c2b2313b93a1dd9391
Source dataset
uspto-grants-2012_05
Patent number
US08188120B2

Reaction notes

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