Home Cart 0 Sign in  

[ CAS No. 152803-24-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 152803-24-2
Chemical Structure| 152803-24-2
Structure of 152803-24-2 * Storage: {[proInfo.prStorage]}

Quality Control of [ 152803-24-2 ]

Related Doc. of [ 152803-24-2 ]

SDS
Alternatived Products of [ 152803-24-2 ]
Alternatived Products of [ 152803-24-2 ]

Product Details of [ 152803-24-2 ]

CAS No. :152803-24-2 MDL No. :MFCD11044307
Formula : C6H4N2O Boiling Point : 394.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :120.11 g/mol Pubchem ID :15342142
Synonyms :

Safety of [ 152803-24-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 152803-24-2 ]

  • Upstream synthesis route of [ 152803-24-2 ]
  • Downstream synthetic route of [ 152803-24-2 ]

[ 152803-24-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 298204-74-7 ]
  • [ 152803-24-2 ]
YieldReaction ConditionsOperation in experiment
95% at 200℃; for 2 h; A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid.LCMS: m/z 120,94 (M+H+).1H MR: δΗ ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.).
95% With pyridine hydrochloride In water at 200℃; for 2 h; Example 11a
5-hydroxynicotinonitrile
A mixture of 1 g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200° C. for 2 hours.
The crude reaction product is diluted in a water fraction several times with diethyl ether.
The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether.
The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid.
LCMS: m/z 120.94 (M+H+).
1H NMR: δH ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.).
95% at 200℃; for 2 h; A mixture of 1g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120,94 (M+H+). 1H NMR: δH ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.)
95% at 200℃; for 2 h; Example 11a: 5-hydroxynicotinonitrile A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120.94 (M+H+). 1H NMR: δΗ ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.).
95% at 200℃; for 2 h; Example 11a: 5-hydroxynicotinonitrile A mixture of lg of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120.94 (M+H+). 1H NMR: δΗ ppm (400 MHz, DMSO): 10.79 (s, 1H), 8.46 (s, 1H, CHarom.), 8.42 (s, 1H, CHarom.), 7.60 (s, 1H, CHarom.).
95% at 200℃; for 2 h; A mixture of 1g of 5-methoxynicotinonitrile (7.46 mmol) and 8.62 g of pyridine hydrochloride is heated at 200°C for 2 hours. The crude reaction product is diluted in a water fraction several times with diethyl ether. The aqueous phase is basified by adding sodium bicarbonate and then extracted again with diethyl ether. The organic phase is dried and then concentrated to yield 850 mg of 5-hydroxynicotinonitrile (95percent) in the form of a beige solid. LCMS: m/z 120,94 (M+H+). 1H NMR: δH ppm (400 MHz, DMSO): 10,79 (s, 1H), 8,46 (s, 1H, CHarom.), 8,42 (s, 1H, CHarom.), 7,60 (s, 1H, CHarom.)

Reference: [1] Patent: WO2012/101239, 2012, A1, . Location in patent: Page/Page column 74
[2] Patent: US2013/85144, 2013, A1, . Location in patent: Paragraph 0394; 0395; 0396
[3] Patent: EP2689778, 2014, A1, . Location in patent: Paragraph 0238
[4] Patent: WO2014/16433, 2014, A1, . Location in patent: Page/Page column 73
[5] Patent: WO2014/16434, 2014, A1, . Location in patent: Page/Page column 72
[6] Patent: EP2689779, 2014, A1, . Location in patent: Paragraph 0297-0299
  • 2
  • [ 402718-29-0 ]
  • [ 152803-24-2 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate; caesium carbonate In water at 120℃; for 16 h; 25 mL of the reaction flask was added hydrazine hydrate (0.25 mmol)5-Cyano-pyridine-3-boronic acid pinacol ester (0.5mmol),Cesium carbonate (1.0 mmol),Water (2.5 mmol)And polyethylene glycol-2000 (2.0 g).The reaction mixture was reacted at 120 ° C until the reaction was complete.The reaction mixture was cooled to room temperature,The product was isolated by column chromatography after evaporation of the solvent under reduced pressure,Yield 85percent.
Reference: [1] Patent: CN103936538, 2017, B, . Location in patent: Paragraph 0073; 0081; 0082
  • 3
  • [ 74115-13-2 ]
  • [ 152803-24-2 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 135℃; for 5 h;
Stage #2: With ammonium hydroxide In water at 0℃; for 1 h;
5-Hydroxy-nicotinonitrile (2) (1199) A mixture of 5-bromo-pyridin-3-ol (9.94 mL, 54.0 mmol) and CuCN (7.4 g, 82.62 mmol) in DMF (20 mL) was heated at 135° C. for 5 hour. DMF was removed under reduced pressure, the residue was diluted with NH4OH (10 mL) at 0° C. The mixture was bubbled with ammonia gas for 1 hour, cooled to 0° C. and acidified with conc. HCl (35 mL) until pH reached to 4. The resulting mixture was extracted with EtOAc (5×100 mL). The organic layer was washed with water (2×100 mL) and brine (2×100 mL) solution, dried over anhydrous Na2SO4, filtered, and concentrated to give yellow solid. Purification was accomplished by flash chromatography on silica gel using 5-25percent EtOAc/hexanes gradient elution to yield the title compound (2.5 g, 39percent) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.78 (s, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.41 (d, J=2.7 Hz, 1H), 7.61-7.57 (m, 1H).
Reference: [1] Patent: US2015/291629, 2015, A1, . Location in patent: Paragraph 1199
[2] Patent: WO2012/37782, 2012, A1, . Location in patent: Page/Page column 42; 57
  • 4
  • [ 74115-13-2 ]
  • [ 544-92-3 ]
  • [ 152803-24-2 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 20, p. 3539 - 3542
Historical Records

Related Functional Groups of
[ 152803-24-2 ]

Nitriles

Chemical Structure| 298204-74-7

[ 298204-74-7 ]

5-Methoxynicotinonitrile

Similarity: 0.92

Chemical Structure| 87032-82-4

[ 87032-82-4 ]

3-Hydroxyisonicotinonitrile

Similarity: 0.85

Chemical Structure| 100-54-9

[ 100-54-9 ]

Nicotinonitrile

Similarity: 0.75

Chemical Structure| 1256835-79-6

[ 1256835-79-6 ]

6-Chloro-5-methoxynicotinonitrile

Similarity: 0.74

Chemical Structure| 932-35-4

[ 932-35-4 ]

3-Hydroxypicolinonitrile

Similarity: 0.73

Alcohols

Chemical Structure| 87032-82-4

[ 87032-82-4 ]

3-Hydroxyisonicotinonitrile

Similarity: 0.85

Chemical Structure| 51035-70-2

[ 51035-70-2 ]

5-(Hydroxymethyl)pyridin-3-ol

Similarity: 0.79

Chemical Structure| 1060804-48-9

[ 1060804-48-9 ]

5-Hydroxynicotinaldehyde

Similarity: 0.78

Chemical Structure| 1121-19-3

[ 1121-19-3 ]

4-Methylpyridin-3-ol

Similarity: 0.76

Chemical Structure| 932-35-4

[ 932-35-4 ]

3-Hydroxypicolinonitrile

Similarity: 0.73

Related Parent Nucleus of
[ 152803-24-2 ]

Pyridines

Chemical Structure| 298204-74-7

[ 298204-74-7 ]

5-Methoxynicotinonitrile

Similarity: 0.92

Chemical Structure| 87032-82-4

[ 87032-82-4 ]

3-Hydroxyisonicotinonitrile

Similarity: 0.85

Chemical Structure| 51035-70-2

[ 51035-70-2 ]

5-(Hydroxymethyl)pyridin-3-ol

Similarity: 0.79

Chemical Structure| 1060804-48-9

[ 1060804-48-9 ]

5-Hydroxynicotinaldehyde

Similarity: 0.78

Chemical Structure| 1121-19-3

[ 1121-19-3 ]

4-Methylpyridin-3-ol

Similarity: 0.76