Sodium Carbonate → 5-amino-2-(cyclopropylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1814711Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=[C:7]3[C:6]2=[O:18])[CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH:1]1([CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=[C:7]3[C:6]2=[O:18])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

N-Cyclopropylmethyl-4-nitrophthalimide (6.0 g, 24 mmol) in methanol (200 mL) was added dropwise over 30 min to a solution of sodium dithionite (27.0 g, 156 mmol) and sodium carbonate (13.0 g, 125 mmol) in water (200 mL) while the temperature was maintained at 70° C. The mixture was stirred at 70° C. for an additional 50 min before it was allowed to cool to room temperature. The reaction volume was then reduced to one-third by rotary evaporation. Water (400 mL) was added, and the suspension extracted with ethyl acetate (2×450 mL). The combined organic solutions were dried with anhydrous MgSO4. Solvent was then removed by rotary evaporation to afford 2.52 g (49%) of pure N-cyclopropylmethyl-4-aminophthalimide as a powder.

Workup

temperatureto cool to room temperature
customThe reaction volume was then reduced to one-third by rotary evaporation
additionWater (400 mL) was added
extractionthe suspension extracted with ethyl acetate (2×450 mL)
dry with materialThe combined organic solutions were dried with anhydrous MgSO4
customSolvent was then removed by rotary evaporation

Sources & evidence

ORD record: ord-4140726fa8b0476099137fa93af1ce34
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875760B2

Reaction notes

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