ChemicalBook CAS DataBase List 4-AMINO-N-METHYLPHTHALIMIDE

4-AMINO-N-METHYLPHTHALIMIDE synthesis

6synthesis methods

Product Name:4-AMINO-N-METHYLPHTHALIMIDE
CAS Number:2307-00-8
Molecular formula:C9H8N2O2
Molecular Weight:176.17

3676-85-5
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$45.00/1g

74-88-4
348 suppliers
$15.00/10g

2307-00-8
172 suppliers
$6.00/250mg

Yield: 92%

Reaction Conditions:

Stage #1:4-aminophthalimide with potassium hydroxide in N,N-dimethyl-formamide at 20; for 2 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 18 h;

Steps:

5-Amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione (11a; ZHAWOC3444):
Potassiumhydroxide (0.35 g,6.17 mmol) was added to a solution of 4-aminophthalimide 10 (1.00 g, 6.17 mmol) in dimethylformamide(30 mL) and the mixture was stirred at ambient temperature for 2 h. Iodomethane (0.88 g, 6.17 mmol) wasadded and it was stirred for another 18 h at the same temperature. Water (50 mL) and ethyl acetate (50 mL)was added and the resulting phases were separated. The organic phase was washed with brine, driedover sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient:0-100% ethyl acetate in cyclohexane) afforded the title compound 11a as a yellow solid (1.00 g, 92% yield):1H-NMR (DMSO-d6): δ = 7.46 (d, J = 8.24 Hz, 1H), 6.90 (d, J = 2.00 Hz, 1H), 6.77 (dd, J = 8.24 Hz, 2.00 Hz,1H), 6.42 (br. s, 2H), 2.94 (s, 3H) ppm. 13C-NMR (DMSO-d6): δ = 168.87, 168.57, 155.27, 135.10, 125.17,117.33, 116.84, 107.42, 23.83 ppm. MS (m/z): 177 [M+ H]+.

References:

Fischer, Thomas;Riedl, Rainer [Molecules,2017,vol. 22,# 9]

41663-84-7 Synthesis