3-N-PHTHALOYLGLYAMINOMETHYL ANILINE synthesis

5synthesis methods

Product Name:3-N-PHTHALOYLGLYAMINOMETHYL ANILINE
CAS Number:77147-14-9
Molecular formula:C15H12N2O2
Molecular Weight:252.27

2-[(3-nitrophenyl)methyl]isoindole-1,3-dione

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Yield:77147-14-9 62%

Reaction Conditions:

Stage #1: 2-(3-nitrobenzyl)isoindoline-1,3-dionewith tin(II) chloride dihdyrate in ethanol; for 6 h;Reflux;
Stage #2: with water;sodium hydroxide in ethyl acetate; for 0.5 h;Cooling with ice;

Steps:

67.2

14.420 g 2-(3-Nitro-benzy.)-isoindole-1 ,3-dione (obtained in Step 1 , 51.10 mmol) was dissolved in 250 cm³ of ethyl-alcohol and 46.108 g SnCI₂ dihydrate (204.35 mmol) was added in portions. The reaction mixture was refluxed for 6 hours. Then the mixture was evaporated under reduced preasure, 300 cm³ of 2N NaOH and 200 cm³ of ethyl-acetate was added and it was stirred for 30 minutes vigrously while it was being cooled in an ice bath. The precipitated solid was filtered off on a Buchner funel and washed well with ethyl-acetate. Filtrate was separated and extracted further three times with 150 - 150 cm³ ethyl-acetate. The combined organic layer was washed with brine, dried over MgS0₄, decolorized with activated carbon and evaporated to dryness. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as an off- white solid. Yield: 7.950 g (62%). Ret. time: 2.42 min., (M+H)⁺ = 253; ¹HNMR (DMSO-d₆, 300 MHz), δ (ppm): 7.87 (m, 4H), 6.93 (t, J=7.62 Hz, 1 H), 6.42 (m, 3H), 5.04 (bs, 2H), 4.60 (s, 2H).

References:

WO2011/77171,2011,A1 Location in patent:Page/Page column 32