5-Cyanophthalide synthesis
- Product Name:5-Cyanophthalide
- CAS Number:82104-74-3
- Molecular formula:C9H5NO2
- Molecular Weight:159.14
265137-37-9
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82104-74-3
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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
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82104-74-3
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82104-74-3
487 suppliers
$8.00/5g