5-CHLORO-2-HYDROXY-3-NITRO-BENZALDEHYDE synthesis

Yield:16634-90-5 61.7%

Reaction Conditions:

with sulfuric acid;nitric acid at 0; for 1.16667 h;

Steps:

174 Synthesis of 174.1.
I Into a 100-mL 3-necked round-bottom flask, was placed 5-chloro- 2-hydroxybenzaldehyde (10 g, 63.87 mmol, 1 equiv). This was followed by the addition of H2SO4 (15 mL, 281.41 mmol, 4.41 equiv) at 0^oC.To this was added HNO3 (6 mL, 133.78 mmol, 2.09 equiv) dropwise with stirring at 0^oC in 1 hr. The resulting solution was stirred for 10 min at 0^oC in an ice/salt bath. The reaction was then quenched by the addition of 200 mL of water/ice. The resulting solution was extracted with 3x100 mL of dichloromethane concentrated under vacuum. The crude product was re-crystallized from EA/PE in the ratio of 1:3. This resulted in 7.946 g (61.7%) of 174.1 as a yellow solid.

References:

NIMBUS ARTEMIS, INC.;LEIT DE MORADEI, Silvana Marcel;THERRIEN, Eric WO2020/97408, 2020, A1 Location in patent:Paragraph 00574

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