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CAS No. :1601-18-9 MDL No. :MFCD01719291
Formula : C20H18ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OKHORWCUMZIORR-UHFFFAOYSA-N
M.W : 371.81 Pubchem ID :15339
Synonyms :
Chemical Name :Methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate

Safety of [ 1601-18-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1601-18-9 ]

* 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.

  • Upstream synthesis route of [ 1601-18-9 ]
  • Downstream synthetic route of [ 1601-18-9 ]

[ 1601-18-9 ] Synthesis Path-Upstream   1~14

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YieldReaction ConditionsOperation in experiment
84%
Stage #1: With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane for 0.166667 h; Inert atmosphere
Stage #2: for 12 h; Inert atmosphere
General procedure: Indomethacin (1 eq.) and BOP-Cl (1 eq.) were suspended in dichloromethane (20 mL/g acid), NEt3 (2 eq.) was slowly added and the mixture stirred for 10 min. The corresponding alcohol (4 eq., and 1 eq. for 2i) was added and the mixture stirred for at least 12 h. The solvent was evaporated and the solid was purified by column chromatography with a mixture of hexanes (80-100 °C) and ethyl acetate (3:1). The solvent was removed under reduced pressure to yield the corresponding ester as slightly yellow solids.
79% at 75℃; for 4 h; Cooling with ice Indomethacin (3.94g, 10mmol) dissolved in 50 ml methanol, and ice dropping under the conditions of 2.4g acetyl chloride. Is omitted, 75oC refluxing 4 hours, evaporate methanol and the remaining acetyl chloride, recrystallization with ethyl ether to obtain white crystal. Yield: 79percent,
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4830 - 4837
[2] Pharmazie, 2003, vol. 58, # 2, p. 99 - 103
[3] Patent: CN105418480, 2016, A, . Location in patent: Paragraph 0031
[4] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 745 - 762
[5] European Journal of Pharmaceutical Sciences, 2001, vol. 14, # 4, p. 301 - 311
[6] Journal of Medicinal Chemistry, 2000, vol. 43, # 15, p. 2860 - 2870
[7] Angewandte Chemie - International Edition, 2017, vol. 56, # 47, p. 14948 - 14952[8] Angew. Chem., 2017, vol. 129, # 47, p. 15144 - 15148,5
[9] Medicinal Chemistry Research, 2012, vol. 21, # 1, p. 16 - 36
[10] Patent: US9808443, 2017, B1, . Location in patent: Sheet 1
[11] Molecules, 2018, vol. 23, # 6,
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Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2616 - 2619
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 19, p. 2263 - 2268
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Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 3, p. 909 - 914
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Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056
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Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056
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Reference: [1] Organic Letters, 2018, vol. 20, # 13, p. 4052 - 4056
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Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2616 - 2619
  • 8
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Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2616 - 2619
  • 9
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Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 4, p. 621 - 622
  • 10
  • [ 1076-74-0 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 19, p. 2263 - 2268
  • 11
  • [ 67-56-1 ]
  • [ 53-86-1 ]
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Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 4, p. 621 - 622
  • 12
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Reference: [1] Journal of Organometallic Chemistry, 1996, vol. 524, # 1-2, p. 87 - 93
  • 13
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  • [ 21909-54-6 ]
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YieldReaction ConditionsOperation in experiment
70% With hydrazine hydrate In ethanol for 30 h; Reflux The methyl ester of indomethacin (0.01 mol) and hydrazine hydrate (99percent) (0.2 mol) in presence of absolute ethanol (50 mL) were refluxed for 30 h. The reaction mixture was concentrated by using rota vapor and poured in a beaker containing ice while stirring and kept for 4 h at room temperature.The solid was separated out by filtration. The product was dried and recrystallized from ethanol.The product was carefully checked by thin layer chromatography. Two compounds were isolated by column chromatography by using different fractions of n-hexane and ethyl acetate. The first compound was 2-(6-methoxy-2-methyl-1H-indol-3-yl) acetohydrazide compound (1) and was obtained as the major product. The second compound, 4-chlorobenzohydrazide (2) was obtained as minor product. Both the compounds were fully characterized by the spectral data. 2-(6-methoxy-2-methyl-1H-indol-3-yl) acetohydrazide (1). Color: white; Yield: 70percent; m.p.: 168–170 °C; UV max (Methanol) = 280 nm; 1H-NMR (500 MHz, DMSO-d6): δ = 2.38 (3H, s, CH3), 3.54 (2H, s,CH2), 3.80 (3H, s, OCH3), 4.26 (2H, s, NH2, D2O exchg.), 6.67 (1H, d, J = 8.5 Hz, Ar–H), 7.16 (2H, d,J = 7.5 Hz, Ar–H), 9.16 (1H, s, NH, D2O exchg.), 10.62 (1H, s, CONH, D2O exchg.); 13C-NMR (125 MHz,DMSO-d6): δ = 12.0 (CH3), 30.2 (CH2), 55.8 (OCH3), 101.1, 105.1, 109.8, 110.0, 111.7, 128.0, 129.3, 129.7,130.6, 134.3, 153.4, 170.8 (C=O); ms: m/z = 233.11 [M]+, 234.07 [M + 1]+; Analysis: C12H15N3O2 for,calcd. C 61.79, H 6.48, N 18.01percent; found C 61.58, H 6.46, N 18.05percent. 4-Chlorobenzohydrazide (2). Color: white; Yield: 20percent; m.p.: 148–150 °C; UV max (Methanol) = 230 nm;1H-NMR (500 MHz, DMSO-d6): δ = 4.53 (2H, s, NH2, D2O exchg.), 7.52 (2H, d, J = 8.5 Hz, Ar–H), 7.84(2H, d, J = 8.5 Hz, Ar–H), 9.87 (1H, s, CONH, D2O exchg.); 13C-NMR (125 MHz, DMSO-d6): δ = 128.86,129.32, 132.50, 136.25, 165.29; MS: m/z = 170.45 [M]+; Analysis: C7H7N2OCl for, calcd. C 49.28, H 4.14,N 16.42percent; found C 49.37, H 4.12, N 16.46percent.
Reference: [1] Molecules, 2018, vol. 23, # 6,
[2] Patent: US9808443, 2017, B1, . Location in patent: Page/Page column 6
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Reference: [1] Pharmazie, 2003, vol. 58, # 2, p. 99 - 103
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