Hydrochloric Acid → Isoindolin-5-amine hydrochloride

HRID 491949Notes

Reaction equation

HRID 491949 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.[ClH:20]>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.[ClH:20]

Participants

5

Reactant 2

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

Product 1

HCID 22240398Isoindolin-5-amine hydrochlorideYield 40.5%

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-3d1d552079a64b908c774f8a4a1726d5
Source dataset
uspto-grants-2009_05
Patent number
US07531535B2

Reaction notes

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