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Chemistry
Heterocyclic Building Blocks
Pyridines
6-(tert-Butyl)nicotinaldehyde
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Pyridines
Aldehydes

[ CAS No. 391900-69-9 ]

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Product Details of [ 391900-69-9 ]

CAS No. :391900-69-9 MDL No. :MFCD09029652
Formula : C10H13NO Boiling Point : 250.7±28.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :163.22 g/mol Pubchem ID :-
Synonyms :

Safety of [ 391900-69-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 391900-69-9 ]

* 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 [ 391900-69-9 ]

[ 391900-69-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 100-55-0 ]
  • [ 75-98-9 ]
  • [ 391900-69-9 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 3-hydroxymethylpyridin; Trimethylacetic acid With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 20℃; for 2h; Stage #2: With ammonium hydroxide In water 18 3-Pyridinemethanol (2.2 g, 20.2 mmol), pivalic acid (10.3 g, 100.8 mmol) and silver nitrate (0.68, 4.0 mmol) were suspended in 10% aqueous H2SO4 (20 ml). Ammonium persulfate (9.2 g, 40.3 mmol) in H2O (40 ml) was added to the mixture. The mixture was stirred at r.t. for 2.0 h. NH4OH was added until pH=9. The product was extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (Pet. Ether/EtOAc 70:30) to give the title substance in 43% yield.1H NMR (CDCl3) δ 10.08 (s, IH), 9.01 (bs, IH), 8.10 (m, IH), 7.51 (d, J=8.4 Hz, IH), 1.40 (s, 9H).
43% Stage #1: 3-hydroxymethylpyridin; Trimethylacetic acid With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 20℃; for 2h; Stage #2: With ammonium hydroxide In water 85 6-tert-Butylnicotinaldehyde 3-Pyridinemethanol (2.2 g, 20.2 mmol), pivalic acid (10.3 g, 100.8 mmol) and silver nitrate (0.68, 4.0 mmol) were suspended in 10% aqueous H2SO4 (20 ml). Ammonium persulfate (9.2 g, 40.3 mmol) in H2O (40 ml) was added to the mixture. The mixture was stirred at r.t. for 2.0 h. NH4OH was added until pH=9. The product was extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (Pet. Ether/EtOAc 70:30) to give the title substance in 43% yield. 1H NMR (CDCl3) δ 10.08 (s, 1H), 9.01 (bs, 1H), 8.10 (m, 1H), 7.51 (d, J=8.4 Hz, 1H), 1.40 (s, 9H).
35% With ammonium persulfate; sulfuric acid; silver nitrate In water at 20℃; for 2h; 1.1 Step-1 : [00159] Preparation of 6-(tert-butyl)nicotinaldehyde 2: To a stirred solution of pyridin-3-yl-methanol (1 , 0.5 g, 4.58 mmol), pivalic acid (2.34 g, 22.9 mmol) and silver nitrate (0.155 g, 0.91 mmol) in 10% aqueous sulfuric acid solution (4.5 mL) was added a solution of ammonium persulfate (2.09 g, 9.16 mmol) in water (10 mL). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was basified to pH 9 with aqueous ammonia and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography using 20% ethyl acetate in hexane to afford the title compound 6-(tert-butyl)nicotinaldehyde (2, 0.26 g, 35%) as a pale yellow liquid. Calculated (M+H): 164.1 ; Found (M+H): 164.1
31% With ammonium peroxydisulfate; sulfuric acid; silver nitrate at 25℃; for 2h;

Reference： [1]Current Patent Assignee: RESPIRATORIOUS - WO2010/97410, 2010, A1 Location in patent: Page/Page column 114
[2]Current Patent Assignee: RESPIRATORIOUS - US2012/40942, 2012, A1 Location in patent: Page/Page column 52
[3]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2018/119374, 2018, A1 Location in patent: Paragraph 00159
[4]Doherty, Elizabeth M.; Fotsch, Christopher; Bo, Yunxin; Chakrabarti, Partha P.; Chen, Ning; Gavva, Narender; Han, Nianhe; Kelly, Michael G.; Kincaid, John; Klionsky, Lana; Liu, Qingyian; Ognyanov, Vassil I.; Tamir, Rami; Wang, Xianghong; Zhu, Jiawang; Norman, Mark H.; Treanor, James J. S. [Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 71 - 90]

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