[ CAS No. 15733-89-8 ]

{[proInfo.proName]}

Quality Control

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc.

SDS

Product Details

CAS No. :15733-89-8MDL No. :MFCD00023942
Formula :C19H27IN4O3InChI Key :MFSHNFBQNVGXJX-UHFFFAOYSA-N
M.W :486.35Pubchem ID :85076
Boiling Point :403.6°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 66.4 H-Bond Acceptor Count : 3
XLogP3 : 0.6 H-Bond Donor Count : 2
SP3 : 0.00 Rotatable Bond Count : 1

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H302-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 15733-89-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 141-82-2 ]
  • [ 91-56-5 ]
  • [ 15733-89-8 ]
YieldReaction ConditionsOperation in experiment
97.3% for 6.00 h; Reflux; Large scale 400 kg of recovered glacial acetic acid was placed in a 1000 L reactor and 100 kg of isatin, 160 kg of malonic acid, and 15 kg of sodium acetate were added under stirring. The mixture was heated to reflux and refluxed for 6 hours. After the reaction is completed, the acetic acid is distilled off under reduced pressure. 300 kg of deionized water are added to stir the crystals. The filtered solids are first washed with cold 30 kg glacial acetic acid and then rinsed with cold 30 kg methanol to obtain 2-hydroxy-. 4-Carboxyquinoline wet product, after filtering and drying at 45-70°C for 24 hours,125 kg of 2-hydroxy-4-carboxyquinoline was obtained with a yield of 97.3percent and a liquid phase purity of 99.6percent.
40% for 16.00 h; Reflux A stirred suspension of isatin, also called 1H-indole-2,3-dione, available from Sigma-Aldrich, (3.80 g, 25 mmol) and malonic acid (8.06 g, 77 mmol) in acetic acid (150 ml) was refluxed for 16 h. Acetic acid was removed under reduced pressure, the residue was suspended in water (150 ml), filtered and washed with water (100 ml) to give a brown solid. The solid was stirred in NaHCO3 saturated aqueous solution (200 ml) and the insoluble material was filtered off. The filtrate was acidified to pH 1-2 withconcentrated HCl and the precipitate was filtered, washed with water and dried to obtainthe desired product as a grey solid (2.2 g, 11.6 mmol, Yield 40percent). 1H NMR (500 MHz; d6-DMSO) δ 6.87 (5, 1H), 7.23 (ddd, 1H, J= 1.2 Hz, J= 7.2 Hz, J=8.3 Hz), 7.41 (dd, 1H, J= 0.7 Hz, J= 8.3 Hz), 7.55 (ddd, 1H, J= 1.4 Hz, J= 7.2 Hz, J=8.4 Hz), 8.15 (dd, 1H, J= 1.2 Hz, J= 8.3 Hz), 12.13 (brs, 1H) ppm. Purity by LCMS (UV Chromatogram, 190-450nm) 90percent, rt = 2.96 min m/z 190 (M+H)+
40% for 16.00 h; Reflux Preparation 10
2-hydroxyquinoline-4-carboxylic acid
A stirred suspension of isatin, also called 1H-indole-2,3-dione, available from Sigma-Aldrich, (3.80 g, 25 mmol) and malonic acid (8.06 g, 77 mmol) in acetic acid (150 ml) was refluxed for 16 h.
Acetic acid was removed under reduced pressure, the residue was suspended in water (150 ml), filtered and washed with water (100 ml) to give a brown solid.
The solid was stirred in NaHCO3 saturated aqueous solution (200 ml) and the insoluble material was filtered off.
The filtrate was acidified to pH 1-2 with concentrated HCl and the precipitate was filtered, washed with water and dried to obtain the desired product as a grey solid (2.2 g, 11.6 mmol, Yield 40percent).
1H NMR (500 MHz; d6-DMSO) δ 6.87 (s, 1H), 7.23 (ddd, 1H, J=1.2 Hz, J=7.2 Hz, J=8.3 Hz), 7.41 (dd, 1H, J=0.7 Hz, J=8.3 Hz), 7.55 (ddd, 1H, J=1.4 Hz, J=7.2 Hz, J=8.4 Hz), 8.15 (dd, 1H, J=1.2 Hz, J=8.3 Hz), 12.13 (brs, 1H) ppm.
Purity by LCMS (UV Chromatogram, 190-450 nm) 90percent, rt=2.96 min, m/z 190 (M+H)+
Reference: [1] Patent: CN108101842, 2018, A. Location in patent: Paragraph 0021; 0023
[2] Synthetic Communications, 2005, vol. 35, # 17, p. 2243 - 2250
[3] Patent: WO2013/153357, 2013, A1. Location in patent: Page/Page column 44
[4] Patent: US2015/45354, 2015, A1. Location in patent: Paragraph 0271-0274
[5] Chemische Berichte, 1914, vol. 47, p. 358
[6] Journal of the Chemical Society, 1926, p. 2908
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1727
  • 2
  • [ 574-17-4 ]
  • [ 15733-89-8 ]
Reference: [1] Synthetic Communications, 2005, vol. 35, # 17, p. 2243 - 2250
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 1, p. 117 - 128
[3] Archiv der Pharmazie (Weinheim, Germany), 1899, vol. 237, p. 687
[4] Journal of the Chemical Society, 1926, p. 2908
[5] Helvetica Chimica Acta, 1957, vol. 40, p. 499
[6] Journal of the Chemical Society, 1926, p. 2908
[7] Journal of the Chemical Society, 1926, p. 2908
  • 3
  • [ 5467-57-2 ]
  • [ 157915-68-9 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2714,2716
  • 4
  • [ 910035-64-2 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 5301,5303
  • 5
  • [ 65112-88-1 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 5301,5303
  • 6
  • [ 67520-95-0 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 5301,5303
  • 7
  • [ 91-56-5 ]
  • [ 15733-89-8 ]
Reference: [1] Helvetica Chimica Acta, 1957, vol. 40, p. 499
[2] Archiv der Pharmazie (Weinheim, Germany), 1899, vol. 237, p. 687
  • 8
  • [ 32375-61-4 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 2908
[2] Journal of the Chemical Society, 1926, p. 2908
  • 9
  • [ 491-35-0 ]
  • [ 15733-89-8 ]
Reference: [1] Patent: US1945067, 1930,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 520
[3] Patent: US1945067, 1930,
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 520
[5] Patent: US1945067, 1930,
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 520
  • 10
  • [ 5467-61-8 ]
  • [ 15733-89-8 ]
Reference: [1] Chemische Berichte, 1938, vol. 71, p. 387,393
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 366
  • 11
  • [ 486-74-8 ]
  • [ 15733-89-8 ]
Reference: [1] Chemische Berichte, 1879, vol. 12, p. 97
[2] Chemische Berichte, 1883, vol. 16, p. 2158
  • 12
  • [ 118-10-5 ]
  • [ 15733-89-8 ]
Reference: [1] Chemische Berichte, 1879, vol. 12, p. 97
  • 13
  • [ 64-19-7 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1669,1670
  • 14
  • [ 7647-01-0 ]
  • [ 910035-64-2 ]
  • [ 15733-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 5301,5303
Related Products
Historical Records