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Chemical Structure| 19501-58-7
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CAS No. :19501-58-7 MDL No. :MFCD00012945
Formula : C7H11ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :FQHCPFMTXFJZJS-UHFFFAOYSA-N
M.W : 174.63 Pubchem ID :2723904
Synonyms :

Safety of [ 19501-58-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19501-58-7 ]

* 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 [ 19501-58-7 ]
  • Downstream synthetic route of [ 19501-58-7 ]

[ 19501-58-7 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 1191-99-7 ]
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  • [ 712-09-4 ]
YieldReaction ConditionsOperation in experiment
58% With sulfuric acid In N,N-dimethyl acetamide at 55℃; for 2 h; 3-(2-Hydroxyethyl)-5-methoxy-lH-indole (5-methyoxytryptophol) (11): No special precaution was taken to excludeambient oxygen from the followingreaction. 4-methoxyphenylhydrazine hydrochloride (1.214 g, 6.95 mmol) was dissolved in a mixture of I 0 mL 0.72 M H2S04 and J 0 mL DMA, and heated to 55 °C. Next, 2,3- d ihydrofuran (0.525 rnL, 6.95 mmol) was added slowly over 2 minutes. The reactionmixture was sti1red at to 55 oc for 2 h after which time it was cooled to ambienttemperature and ex tracted with isopropylacetate (2 x 25 mL). The combined organiclayers were washed with H20 (3 x 20 mL) and saturated NaCl (1 x 20 mL), dried with Na2S04, filtered and concentrated. The crude residue was purified via flashcolwnnchromatography (50:50 ethyl acetate/hexanes) to afford 11 as an orange-red oil
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 23, p. 6888 - 6891[2] Angew. Chem., 2018, vol. 130, # 23, p. 7004 - 7007,4
[3] Organic Letters, 2017, vol. 19, # 7, p. 1504 - 1507
[4] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5489 - 5491
[5] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 363 - 367
[6] Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12910 - 12914[7] Angew. Chem., 2013, vol. 125, # 49, p. 13148 - 13152,5
[8] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6710 - 6717
  • 2
  • [ 13436-46-9 ]
  • [ 19501-58-7 ]
  • [ 712-09-4 ]
Reference: [1] Heterocycles, 2003, vol. 60, # 5, p. 1095 - 1110
  • 3
  • [ 624-45-3 ]
  • [ 19501-58-7 ]
  • [ 7588-36-5 ]
Reference: [1] Patent: US5877202, 1999, A,
[2] Patent: US5639780, 1997, A,
  • 4
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  • [ 7588-36-5 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2616 - 2619
  • 5
  • [ 19501-58-7 ]
  • [ 1601-18-9 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2616 - 2619
  • 6
  • [ 19501-58-7 ]
  • [ 53164-05-9 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
  • 7
  • [ 104-94-9 ]
  • [ 19501-58-7 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With hydrogenchloride; sodium nitrite In water for 1.75 h; Cooling
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.5 h;
To asolution of p-anisidine (4.93 g, 40mmol) in water (12 mL) and conc. HCl (12 mL) was added a solution of sodiumnitrite (3.3 g, 46.40 mmol) in water (10 mL) dropwise at -5 oC overthe period of 15 min. The reaction mixture was stirred for 1.5 h and a solutionof SnCl2 (16.00 g, 84.40 mmol) in conc. HCl (25 mL) was addeddropwise and stirred manually in spite of bulky precipitation. After thereaction mixture was stirred at 0 oC for 30 min, the precipitate wascollected by filtration, washed with water (20 mL), ethanol (12 mL), and Et2O(50 mL) and dried in vacuo to give compound 4 (5.40 g, 31.00 mmol, 77percent) as a pink solid: Rf =0.23 (n-hexane : EtOAc = 2:1); 1H NMR (400MHz, D2O) δ6.94 (2H, d, J = 8.8 Hz), 6.84 (2H, d, J = 8.8Hz), 3.64 (3H, s).
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3322 - 3336
[2] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 1 - 11
[3] Russian Chemical Bulletin, 2005, vol. 54, # 10, p. 2417 - 2424
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4692 - 4696
[5] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5295 - 5308
[6] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10699 - 10706
[7] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[8] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4
[9] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[10] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[11] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[12] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 761 - 766
[13] PLoS ONE, 2015, vol. 10, # 6,
[14] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
[15] Organic and Biomolecular Chemistry, 2016, vol. 14, # 41, p. 9868 - 9873
[16] Journal of the Chinese Chemical Society, 2018, vol. 65, # 5, p. 538 - 547
[17] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 137 - 147
  • 8
  • [ 4346-59-2 ]
  • [ 19501-58-7 ]
Reference: [1] Patent: US2004/116475, 2004, A1, . Location in patent: Page/Page column 21
  • 9
  • [ 1352877-26-9 ]
  • [ 19501-58-7 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 52, p. 10296 - 10303
  • 10
  • [ 696-62-8 ]
  • [ 19501-58-7 ]
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
  • 11
  • [ 104-92-7 ]
  • [ 19501-58-7 ]
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
  • 12
  • [ 89693-83-4 ]
  • [ 19501-58-7 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 13
  • [ 148678-86-8 ]
  • [ 19501-58-7 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 20, p. 3613 - 3624
  • 14
  • [ 459-64-3 ]
  • [ 19501-58-7 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 52, p. 10296 - 10303
  • 15
  • [ 19501-58-7 ]
  • [ 77063-21-9 ]
  • [ 188817-13-2 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7200 - 7214
  • 16
  • [ 19501-58-7 ]
  • [ 18931-60-7 ]
  • [ 188817-13-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365
  • 17
  • [ 19501-58-7 ]
  • [ 618910-07-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 5, p. 717 - 722
  • 18
  • [ 7424-91-1 ]
  • [ 19501-58-7 ]
  • [ 172595-68-5 ]
YieldReaction ConditionsOperation in experiment
97% at 70℃; for 4.5 h; (Intermediate Example 38)
5-Methoxy-1-methyl-1H-indole-3-carboxylic acid
4-Methoxyphenylhydrazine hydrochloride (200 mg) and methyl 3,3-dimethoxypropionate (194 mg) were added to acetic acid (8.0 ml) and stirred for 4.5 hours at 70°C.
The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (eluding solvent; ethyl acetate: n-hexane 1: 5 --> 1: 3) to give methyl 5-methoxy-1H-indole-3-carboxylate (259 mg, Y.: 97percent).
1H NMR; (DMSO-d6) δ (ppm): 3.8 (3H, s), 3.9 (3H, s), 6.8 (1H, dd), 7.4 (1H, d), 7.5 (1H, d), 8.0 (1H, s), 11.8 (1H, brs).
ESI/MS (m/z): 204 (M-H)-.
Reference: [1] Patent: EP1595866, 2005, A1, . Location in patent: Page/Page column 18
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