ChemicalBook CAS DataBase List 5-Cyanophthalide

5-Cyanophthalide synthesis

9synthesis methods

Product Name:5-Cyanophthalide
CAS Number:82104-74-3
Molecular formula:C9H5NO2
Molecular Weight:159.14

5-Cyanophthalide is an important intermediate in the preparation of metastatic breast cancer drug citalopram. Thionyl-chloride in DMF was added in 5-carbamylphthalid in toluene. The reaction mixture was heated at 75 ° C. for 6 hours and purified to obtain 5-Cyanophthalide.

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Yield:82104-74-3 11.9 g (75%)

Reaction Conditions:

in thionyl chloride;water;N,N-dimethyl-formamide;toluene

Steps:

3 Preparation of 5-Cyanophthalide
Example 3 Preparation of 5-Cyanophthalide To a suspension of 4,4-dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline (23.1 g, 0.1 mol) in thionyl chloride (36 mL) is slowly added N,N-dimethylformamide (5 ml). The solution is heated at reflux for 1 hour and then allowed to cool to room temperature over 3 hours. Then toluene (150 mL) is added and the suspension is filtered and washed with toluene (2*50 mL). The wet crystals are taken into deionized water (150 mL) and the pH is adjusted to 8.0 with 25% aqueous ammonia. The solid is filtered and washed with deionized water (2*50 mL) and dried at 60° C. under reduced pressure. Yield: 11.9 g (75%) of an off-white product having a purity (HPLC, peak area)=92%. An analytical pure sample is obtained by crystallisation from acetic acid or toluene. ¹H NMR (DMSO d-6, 500 MHz): 5.48 (2H,s), 8.04 (2H,s+s), 8.22 (1H,s)

References:

H. Lundbeck A/S US2003/13895, 2003, A1