Ammonium Chloride → 4-Amino-2-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]2,3-dihydroisoindol-1-one

HRID 914974Notes

Reaction equation

HRID 914974 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[N+:22]([O-])=O)[C:14]1=[O:25].[Cl-].[NH4+]>CO.O.[Zn]>[NH2:22][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH2:21][N:13]([CH2:12][CH2:11][N:2]1[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]1)[C:14]2=[O:25]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 589581672-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-4-nitro-2,3-dihydroisoindol-1-one

Product 1

HCID 589582214-Amino-2-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]2,3-dihydroisoindol-1-oneYield 91.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 37 (0.38 g, 1.1 mmol) in methanol (6 mL) was added a solution of ammonium chloride (0.13 g, 2.42 mmol) in water (1.5 mL). Zinc powder (0.49 g, 7.4 mmol) was then added portionwise and the resulting mixture was stirred for 2 hours. The solids were filtered and washed with methanol, the filtrate was basified with saturated sodium bicarbonate (aq.), and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 38 (0.31 g, 88%).

Workup

  1. filtrationThe solids were filtered
  2. washwashed with methanol
  3. extractionthe resulting mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20d0830d01c949039f858551436077bf
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

Loading…