Home Cart Sign in  
Chemical Structure| 22931-71-1 Chemical Structure| 22931-71-1

Structure of 22931-71-1

Chemical Structure| 22931-71-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 22931-71-1 ]

CAS No. :22931-71-1
Formula : C13H12ClNO3
M.W : 265.69
SMILES Code : CCOC(=O)C1=C(Cl)C2=CC(OC)=CC=C2N=C1
MDL No. :MFCD00173417
InChI Key :QURGQUFEJWWDRF-UHFFFAOYSA-N
Pubchem ID :304558

Safety of [ 22931-71-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 22931-71-1 ]

* 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 [ 22931-71-1 ]

[ 22931-71-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 77156-78-6 ]
  • [ 22931-71-1 ]
YieldReaction ConditionsOperation in experiment
98% With trichlorophosphate; for 2h;Inert atmosphere; Reflux; A suspension of <strong>[77156-78-6]ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate</strong> (6, 1.65 g, 6.5 mmol) in 10 ml of phosphorus oxychloride was heated for 2 h to reflux. Subsequently the reaction mixture was cooled to room temperature and freed from the excess phosphorus oxychloride under reduced pressure. The remainder was dissolved in ethyl acetate, to this solution warm water was slowly added under vigorous stirring. The phases were separated, the organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to deliver ethyl 4-chloro-6-methoxyquinoline-3-carboxylate (12, 1.7 g, 6.5 mmol, 98 %) which was pure enough to be directly used in the next step. 1H-NMR (CDCl3): delta = 1.47 (t, 3H), 4.00 (s, 3H), 4.51 (q, 2H), 7.48 (dd, 1H), 7.60 (d, 1H), 8.05 (d, 1H), 9.06 (s, 1H). LC-MS: Rt = 1.81 min; MS: m/z = 266 [M+1]+.
97% In trichlorophosphate; Example 1b ethyl 4-chloro-6-methoxyquinoline-3-carboxylate A solution of <strong>[77156-78-6]ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate</strong> (Example 1c, 1.24 g, 5.0 mmol) in POCl3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale-yellow solid (1.29 g, 97%). 1H NMR (400 MHz, DMSO-d6) delta 1.36 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 7.57 (d, J=2.8 Hz, 1H), 7.61 (dd, J=2.8, 8.8 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).
97% With trichlorophosphate; for 3h;Reflux; Inert atmosphere; A solution of <strong>[77156-78-6]ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate</strong> (Example Ac, 1.24 g, 5.0 mmol) in POCI3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale -yellow solid (1.29 g, 97%). .H NMR (400 MHz, DMSO-i¾ delta 1.36 (t, J = 7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J = 7.0 Hz, 2H), 7.57 (d, J = 2.8 Hz, 1H), 7.61 (dd, J = 2.8, 8.8 Hz, 1H), 8.05 (d, J = 8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).
97% With trichlorophosphate; for 3h;Inert atmosphere; Reflux; Example 1b ethyl 4-chloro-6-methoxyquinoline-3-carboxylate A solution of <strong>[77156-78-6]ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate</strong> (Example 1c, 1.24 g, 5.0 mmol) in POCl3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale-yellow solid (1.29 g, 97%). 1H NMR (400 MHz, DMSO-d6) delta 1.36 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 7.57 (d, J=2.8 Hz, 1H), 7.61 (dd, J=2.8, 8.8 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).
97% In trichlorophosphate; Example 1b ethyl 4-chloro-6-methoxyquinoline-3-carboxylate A solution of <strong>[77156-78-6]ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate</strong> (Example 1c, 1.24 g, 5.0 mmol) in POCl3 was refluxed under nitrogen for 3 hrs. The solution was cooled to room temperature and evaporated under reduced pressure. The residue was carefully quenched with ice, and neutralized with 2.0 N NaOH to pH 7. The precipitate was collected by filtration, washed with cold water, and dried under vacuum to give the title compound as a pale-yellow solid (1.29 g, 97%). 1H NMR (400 MHz, DMSO-d6) delta 1.36 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.41 (q, J=7.0 Hz, 2H), 7.57 (d, J=2.8 Hz, 1H), 7.61 (dd, J=2.8, 8.8 Hz, 1H), 8.05 (d, J=8.8 Hz, 1H), 8.97 (s, 1H). MS 266, 268 (MH+).
82% With trichlorophosphate; for 3h;Reflux; General procedure: To the corresponding intermediate 10 (25 mmol), POCl3 (125 mmol) was added slowly and refluxed for 3 h at 105 C. TLC analysis indicated that the reaction was completed. Excess POCl3 was removed under reduced pressure and the crude reaction mass was quenched with crushed ice then neutralized with saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate(3*100 mL). The organic layer was dried over anhy. Na2SO4, filtered and evaporated under reduced pressure to get corresponding desired chloro intermediate.

  • 2
  • [ 7504-94-1 ]
  • [ 22931-71-1 ]
  • 8-methoxy-2-pyrimidin-2-yl-2,5-dihydro-pyrazolo[4,3-<i>c</i>]quinolin-3-one [ No CAS ]
  • 3
  • [ 22931-71-1 ]
  • [ 77156-78-6 ]
  • 4-chloro-6-methoxyquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 2h; To a solution of ethyl 4-chloro-6-methoxyquinoline-3-carboxylate (531 mg, 2 mmol) in THF (4 ml) was added IN NaOH(aq) (2 mL, 2 mmol) at 0 C. The mixture was then warmed to rt and stirred for 2 h. IN HCl(aq) (2 mL, 2 mmol) was added dropwise and then hexane (10 mL) was added. The solid was filtered and washed with small amounto of H20 (1 mL x 3), and then dried to give 4-chloro-6-methoxyquinoline- 3-carboxylic acid (450 mg, 1.42 mmol, 71.0 % yield). This material contained ca. 20-25% of ethyl 4- hydroxy-6-methoxyquinoline-3-carboxylate, which was used for next step without further purification. LC-MS (Method 1): tR= 2.75 min, m/z (M+H)+= 238.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 22931-71-1 ]

Chlorides

Chemical Structure| 77156-85-5

A260876 [77156-85-5]

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 112190-03-1

A196083 [112190-03-1]

Ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 1123169-50-5

A162963 [1123169-50-5]

Methyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.96

Chemical Structure| 27568-05-4

A686878 [27568-05-4]

Ethyl 4-chloro-8-methoxyquinoline-3-carboxylate

Similarity: 0.95

Chemical Structure| 26893-14-1

A332693 [26893-14-1]

Ethyl 4-chloro-6,7-dimethoxyquinoline-3-carboxylate

Similarity: 0.95

Ethers

Chemical Structure| 77156-85-5

A260876 [77156-85-5]

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 112190-03-1

A196083 [112190-03-1]

Ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 1123169-50-5

A162963 [1123169-50-5]

Methyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.96

Chemical Structure| 27568-05-4

A686878 [27568-05-4]

Ethyl 4-chloro-8-methoxyquinoline-3-carboxylate

Similarity: 0.95

Chemical Structure| 26893-14-1

A332693 [26893-14-1]

Ethyl 4-chloro-6,7-dimethoxyquinoline-3-carboxylate

Similarity: 0.95

Esters

Chemical Structure| 77156-85-5

A260876 [77156-85-5]

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 112190-03-1

A196083 [112190-03-1]

Ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 1123169-50-5

A162963 [1123169-50-5]

Methyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.96

Chemical Structure| 27568-05-4

A686878 [27568-05-4]

Ethyl 4-chloro-8-methoxyquinoline-3-carboxylate

Similarity: 0.95

Chemical Structure| 26893-14-1

A332693 [26893-14-1]

Ethyl 4-chloro-6,7-dimethoxyquinoline-3-carboxylate

Similarity: 0.95

Related Parent Nucleus of
[ 22931-71-1 ]

Quinolines

Chemical Structure| 77156-85-5

A260876 [77156-85-5]

Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 112190-03-1

A196083 [112190-03-1]

Ethyl 4-chloro-6-ethoxyquinoline-3-carboxylate

Similarity: 0.99

Chemical Structure| 1123169-50-5

A162963 [1123169-50-5]

Methyl 4-chloro-7-methoxyquinoline-3-carboxylate

Similarity: 0.96

Chemical Structure| 27568-05-4

A686878 [27568-05-4]

Ethyl 4-chloro-8-methoxyquinoline-3-carboxylate

Similarity: 0.95

Chemical Structure| 26893-14-1

A332693 [26893-14-1]

Ethyl 4-chloro-6,7-dimethoxyquinoline-3-carboxylate

Similarity: 0.95