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Chemical Structure| 138173-83-8 Chemical Structure| 138173-83-8

Structure of 138173-83-8

Chemical Structure| 138173-83-8

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Product Details of [ 138173-83-8 ]

CAS No. :138173-83-8
Formula : C10H9NO3
M.W : 191.18
SMILES Code : O=C(C(O1)=CC2=C1C=NC=C2)OCC
MDL No. :MFCD20527951
InChI Key :YIEKKNVBDRSMCX-UHFFFAOYSA-N
Pubchem ID :642130

Safety of [ 138173-83-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 138173-83-8 ]

* 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.

  • Upstream synthesis route of [ 138173-83-8 ]
  • Downstream synthetic route of [ 138173-83-8 ]

[ 138173-83-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 138173-83-8 ]
  • [ 112372-15-3 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h;
Stage #2: With acetic acid In tetrahydrofuran; methanol
b: furo[2,3-clpyridine-2-carboxylic acid:To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate (3.82 g, 19.98 mmol) in water:THF:MeOH (1 : 1 : 1 , 60 mL) was added potassium hydroxide (3.36 g, 59.9 mmol) and the resulting mixture was stirred at ambient temperature for 16 hours. The solvent volume was then reduced to ~20 mL and acetic acid was added until pH ~4. The solids were collected by vacuum filtration, washed twice with water, and dried in a vacuum oven overnight to afford the title compound (2.90 g, 89percent). 1H NMR (DMSO-de): δ 9.09 (s, 1H), 8.47 (d, 1H), 7.81 (dd, 1H), 7.71 (d, 1H), 3.36 (br s, 1H).
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Step 6. To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate (158 g, 0.83 mol) in water:THF:MeOH (1:1:1, 2.4 L) was added KOH (139 g, 2.49 mol). Thereaction mixture was stirred at rt for 16 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH 4. The resulting solids were collected by filtration, washed with water (300 mLx2) and dried in a vacuum oven overnight to give the title compound (101 g, 75percent) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) 6 9.07 (s, 1H), 8,47 (d, J 5.6 Hz, 1H), 7.80 (d, J = 5.2 Hz,1H), 7.61 (s, 1H). MS (ESI+) m/z: 164 [M+F]+
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Step 6. To a solution of ethyl furo[2,3-cjpyridine-2-carboxylate (158 g, 0.83 mol) in water:THF:MeOH (I: 1:1, 2.4 L) was added KOH (139 g, 2.49 mol). Thereaction mixture was stirred at ii for 1 6 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH 4. The resulting solids were collected by filtration, washed with water (300 mLx2) and dried in a vacuum oven overnight to give the title compound (101 g, 75percent) as a pale yellow solid. 1H NMR (400 Mi-Iz, DMSO-d6) 6 9.07 (s, In), 8,47 (d, J 5.6 Hz, I H), 7.80 (d, J = 5.2 Hz,1H), 7.61 (s, IH). MS (ES1-b) ni z: 164 [M+F]+
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Step 6. To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate ( 158 g, 0,83 mol) in water:THF:MeOH (1 : 1 : 1 , 2 4 L) was added KOH ( 139 g, 2.49 mol). The reaction mixture was stirred at rt for 1 6 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH ~ 4. The resulting solids were collected by filtration, washed with water (300 mL> 2) and dried in a vacuum oven overnight to give the title compound ( 101 g, 75percent) as a pale yellow solid. NMR (400 MHz, DMSO-ay δ 9.07 (s, 1 H), 8.47 (d, = 5.6 Hz, 1 H), 7.80 (d, J = 5.2 Hz, 1 H), 7.61 (s, 1 H). MS (ESI+) m. z: 1 64 [M+H] \
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Step 6. To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate (158 g, 0.83 mol) in water:THF:MeOH (1:1:1, 2.4 L) was added KOH (139 g, 2.49 mol). Thereaction mixture was stirred at rt for 16 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH 4. The resulting solids were collected by filtration, washed with water (300 mLx2) and dried in a vacuum oven overnight to give the title compound (101 g, 75percent) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) 6 9.07 (s, 1H), 8,47 (d, J 5.6 Hz, 1H), 7.80 (d, J = 5.2 Hz,1H), 7.61 (s, 1H). MS (ESI+) m/z: 164 [M+F]+
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Intermediate 1: Furo[2,3-clpyridine-2-carboxylic acid [0171] Step 6. To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate (158 g, 0.83 mol) in water:THF:MeOH (1:1:1, 2.4 L) was added KOH (139 g, 2.49 mol). The reaction mixture was stirred at rt for 16 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH 4. The resulting solids were collected by filtration, washed withwater (300 mLx2) and dried in a vacuum oven overnight to give the title compound (101 g, 75percent) as a pale yellow solid. ‘H NMR (400 MHz, DMSO-d6) ö 9.07 (s, 1H), 8.47 (d, J = 5.6 Hz, 1H), 7.80 (d, J = 5.2 Hz, 1H), 7.61 (s, 1H). MS (ESI+) m/z: 164 [M+Hf’.
75% With water; potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; Step 6. To a solution of ethyl furo[2,3-c]pyridine-2-carboxylate (158 g, 0.83 mol) in water:THF:MeOH (1 : 1 : 1, 2.4 L) was added KOH (139 g, 2.49 mol). The reaction mixture was stirred at rt for 16 h and then concentrated to a volume of 750 mL. To this residue was added acetic acid until pH ~ 4. The resulting solids were collected by filtration, washed with water (300 mLx2) and dried in a vacuum oven overnight to give the title compound (101 g, 75percent) as a pale yellow solid. 1H NMR (400 MHz, DMSO-J6) δ 9.07 (s, 1H), 8.47 (d, J = 5.6 Hz, 1H), 7.80 (d, J = 5.2 Hz, 1H), 7.61 (s, 1H). MS (ESI+) m/z: 164 [M+H]+.

References: [1] Patent: WO2012/31197, 2012, A1, . Location in patent: Page/Page column 400-401.
[2] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 128; 129; 130.
[3] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 79; 81.
[4] Patent: WO2013/127269, 2013, A1, . Location in patent: Page/Page column 143.
[5] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 57; 59.
[6] Patent: WO2013/130935, 2013, A1, . Location in patent: Paragraph 0171.
[7] Patent: WO2013/130943, 2013, A1, . Location in patent: Paragraph 0179.
 

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