4-Chloro-5-nitroisoquinoline synthesis
- Product Name:4-Chloro-5-nitroisoquinoline
- CAS Number:53599-88-5
- Molecular formula:C9H5ClN2O2
- Molecular Weight:208.6012
1532-91-8
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Yield:53599-88-5 88%
Reaction Conditions:
with sulfuric acid;potassium nitrate at -5 - 20; for 1 h;
Steps:
16.1
To a solution of 4-chloroisoquinoline 16a (10.0 g, 61 mmol) in 55 mL concentrated sulfuric acid was added a solution of potassium nitrate (7.98 g, 79 mmol) in 69.0 mL concentrated sulfuric acid at -5° C.
The resulting mixture was stirred at 0° C. for 1 h and then stirred at room temperature overnight.
The reaction mixture was poured to 300 mL ice water, adjusted pH to 8 using solid Na2CO3, extracted with EtOAc (200 mL*2).
The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated.
The crude product was purified by silica gel column chromatography (0-100% EtOAc/PE) to give 4-chloro-5-nitroisoquinoline 16b (11.2 g, white solid, yield: 88%).
MS-ESI calc'd. [M+H]+ 209, found 209.
References:
US2017/37050,2017,A1 Location in patent:Paragraph 0240-0242
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