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Chemical Structure| 867267-27-4 Chemical Structure| 867267-27-4

Structure of 867267-27-4

Chemical Structure| 867267-27-4

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Product Details of [ 867267-27-4 ]

CAS No. :867267-27-4
Formula : C9H11NO4
M.W : 197.19
SMILES Code : O=CC1=C(OCOC)C=NC(OC)=C1
MDL No. :MFCD24677902
InChI Key :CLADBSZPHROUKB-UHFFFAOYSA-N
Pubchem ID :12180720

Safety of [ 867267-27-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 867267-27-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 867267-27-4 ]

[ 867267-27-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 867267-27-4 ]
  • [ 867267-28-5 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogenchloride; In tetrahydrofuran; water; at 50℃; for 0.5h; Step 3 ;To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (10 g, 0.05 mol) in THF (100 mL) was added 3 N HCl (150 mL). The reaction was stirred at 50 C. for 30 min, cooled to rt, and diluted with water (100 mL). The mixture was neutralized to pH 7-8 and extracted with EtOAc (200 mL) three times. The organic layer was dried over Na2SO4 and concentrated to give 5-hydroxy-2-methoxyisonicotinaldehyde (4.2 g, 55%) as a yellow solid. 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H).
With hydrogenchloride; In tetrahydrofuran; at 50℃; for 0.5h; [0172] To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (10 g, 0.05 mol) in THF (100 mL) was added 3 N HC1 (150 mL). The reaction was stirred at 50 C for 30 mm, cooled to rt, and diluted with water (100 mL). The mixture was neutralized to pH 7-8 and extracted with EtOAc (200 mL) three times. The organic layer was dried over Na2SO4 andconcentrated to give 5-hydroxy-2-methoxyisonicotinaldehyde (4.2 g, 55%) as a yellow solid. 1H NMR (400 MHz; DMSO) δ= l0.31(s, 1 H), 8.03 (s, 1 H), 6.89 (s, 1 H), 3.80 (s, 3 H).
With hydrogenchloride; In tetrahydrofuran; at 50℃; for 1h; [02601 To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol,1 eq.) in THF (150 mL) was added HC1 (3 N, 250 mL, 4.4 eq.). The reaction was stirred at 50 Cfor 1 h, cooled to rt, and diluted with water (500 mL). The mixture was neutralized to pH 7-8with solid K2C03. The pale yellow solid was collected, washed with water, and dried to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%) as a pale yellow solid. 1H NMR (400 MHz; DMSO) = 10.31 (s, 1 H), 8.03 (s, 1 H), 6.89 (s, 1 H), 3.80 (s, 3 H). LRMS (M+H+) m/z 154.0.
17.9 g With hydrogenchloride; water; In tetrahydrofuran; at 50℃; for 1h; To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol) in THF (150 mL) was added HCl (3 N, 250 mL). The reaction was stirred at 50 C. for 1 h, cooled to RT and diluted with water (500 mL). The mixture was neutralized to pH 7-8 with solid K2CO3. The pale yellow solid was collected, washed with water, and dried in vacuum oven (40 C.) overnight to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%). 1H NMR (400 MHz; DMSO)=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H); MS (ESI) m/z 154.0 [M+H]+.
600 mg With hydrogenchloride; In tetrahydrofuran; at 70℃; for 2h; To a stirred solution of 2-methoxy-5-methoxymethoxypyridine-4-carbaldehyde (1.5 g, 7.61 mmol) in THF (3 mL) was added 3N HC1 (15 mL) at room temperature and the reaction mixture was heated to 70C for 2 hr. The reaction mixture was cooled under ice bath, neutralizedwith K2C03 and extracted with ethyl acetate (50 mL x 2). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide the crude product which was purified by column chromatography to afford 600 mg of 5-hydroxy-2-methoxy-pyridine-4- carbaldehyde. ‘H-NMR (DMSO-d6, 400 MHz): ö 10.33 (s, 1H), 10.30 (s, 1H), 8.02 (s, 1H), 6.88 (s, 1H), 3.79 (s, 3H).

  • 2
  • [ 867267-27-4 ]
  • [ 867267-28-5 ]
  • [ 1446321-92-1 ]
YieldReaction ConditionsOperation in experiment
74.6% With hydrogenchloride; In tetrahydrofuran; Step 3: To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol) in THF (150 mL) was added HCl (3 N, 250 mL). The reaction was stirred at 50 C. for 1 h, cooled to RT and diluted with water (500 mL). The mixture was neutralized to pH 7-8 with solid K2CO3. The pale yellow solid was collected, washed with water, and dried in vacuum oven (40 C.) overnight to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%). 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H); MS (ESI) m/z 154.0 [M+H]+.
 

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