ChemicalBook CAS DataBase List 6-CHLORO-5-METHYLPYRIDINE-3-CARBALDEHYDE

6-CHLORO-5-METHYLPYRIDINE-3-CARBALDEHYDE synthesis

5synthesis methods

Product Name:6-CHLORO-5-METHYLPYRIDINE-3-CARBALDEHYDE
CAS Number:176433-43-5
Molecular formula:C7H6ClNO
Molecular Weight:155.58

4394-85-8 Synthesis

4394-85-8
318 suppliers
$6.00/25g

29241-60-9 Synthesis

29241-60-9
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$6.00/1g

6-CHLORO-5-METHYLPYRIDINE-3-CARBALDEHYDE

176433-43-5
78 suppliers
$35.00/500mg

Yield:176433-43-5 79.6%

Reaction Conditions:

Stage #1:5-bromo-2-chloro-3-methylpyridine with isopropylmagnesium chloride in tetrahydrofuran at 0 - 20; for 1 h;
Stage #2:4-morpholinecarboxaldehyde in tetrahydrofuran at 20; for 1 h;

Steps:

1.1.1 Step 1: Preparation of compound 1-2 cc
To a solution of 1-1 (5 g, 24.2 mmol) in THF (200 mL) was added drop-wise isopropyl magnesium chloride (12.7 mL, 25.5 mmol) in THF at 0° C. The mixture was stirred at room temperature for 1 h. A solution of morpholine-4-carbaldehyde (2.5 mL, 24.2 mmol) in THF (50 ml) was added drop-wise into the mixture slowly and the mixture was stirred at same temperature for 1 h. The solution was poured into ice water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na₂SO₄, filtered concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel chromatography eluted to give product 1-2 (3.0 g, 79.6%). MS m/z [ESI]: 156.0 [M+1].

References:

SUZHOU SINOVENT PHARMACEUTICALS CO., LTD.;WANG, Yonghui;ZHU, Yan;ZHOU, Juan;GAO, Yujun;WANG, Shiqun;WANG, Dong;LIU, Wandeng;SHEN, Ximing;HONG, Binbin;LIU, Tao;WU, Yaodong;LI, Chunqi US2018/271846, 2018, A1 Location in patent:Paragraph 0101; 0102-0104

FullText

887707-21-3 Synthesis