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[ CAS No. 2213-63-0 ]

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Chemical Structure| 2213-63-0
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CAS No. :2213-63-0MDL No. :MFCD00006720
Formula : C8H4Cl2N2 Boiling Point : 269.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :199.04Pubchem ID :16659
Synonyms :

Computed Properties of [ 2213-63-0 ]

TPSA : 25.8 H-Bond Acceptor Count : 2
XLogP3 : 3.1 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 2213-63-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H317-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2213-63-0 ]

  • Upstream synthesis route of [ 2213-63-0 ]
  • Downstream synthetic route of [ 2213-63-0 ]

[ 2213-63-0 ] Synthesis Path-Upstream   1~29

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Reference: [1] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111
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YieldReaction ConditionsOperation in experiment
63% With ammonia In 1-methyl-pyrrolidin-2-one at 80℃; for 3 h; 2-Amino-3-chloroquinoxaline (2a). The compound was synthesized by a slightly modified version of the procedure of Saikachi and Tagami [1] using a reaction temperature of only 80 °C. Compound 1 (8.0 g, 40.2 mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60 mL) and heated to 80 ºC. Then, ammonia gas was bubbled through the hot solution for 3 h while the reaction was monitored by TLC. The crude product was poured into water (100 mL). The precipitate was collected by filtration, dried over CaCl2 and crystallized from chloroform to give 4.8 g (63percent) pale yellow crystals, mp. 137–139 °C. The NMR data are in accordance with a semihydrate. 1H-NMR (CDCl3): δ 1.85 (br, 1 H, 0.5 H2O), 5.53 (br s, 2 H, NH2), 7.47 (td, 3J = 8.3, 6.8, 4J = 1.7 Hz, 1 H, H-6), 7.63 (td, 3J = 8.3, 6.8, 4J = 1.4 Hz, 1 H, H-7), 7.69 (ddd, 3J = 8.3, 4J = 1.5, 5J = 0.5 Hz, 1 H, H-8), 7.86 ppm (ddd, 3J = 8.2, 4J = 1.3, 5J = 0.5 Hz, 1 H, H-5). 13C-NMR (CDCl3): δ 125.4 (CH-6), 126.1 (CH-8), 128.1 (CH-5), 130.6 (CH-7), 137.1, 137.3 (Cq-4a, Cq-3), 140.3 (Cq-8a), 148.7 ppm (Cq-2). MS (EI 70 eV, 165 ºC): m/z (percent) = 181 (30) [M+(37Cl)], 179 (100) [M+(35Cl)], 144 (84), 117 (23), 102 (8), 90 (26), 44 (81). Water was separated by azeotropic distillation with toluene at normal pressure. Residual toluene was removed in vacuum. Anal. Calcd for C8H6ClN3 (179.61 gmol−1): C, 53.50; H, 3.37; N 23.40. Found: C, 53.59; H, 3.40; N 22.96.
53% With ammonium carbonate In N,N-dimethyl-formamide at 60℃; for 72 h; 2, 3-dichloroquinoxaline (4 g, 20 mmol, commercially available from Aldrich) is dissolved in dry DMF (20 ml) and treated with solid (NH4)2CO3 (9.7 g, 101 mmol). The resulting mixture is stirred at 60 0C for 3 days (reaction showed 60 percent completion). The reaction mixture is diluted with water and the product is extracted with EtOAc. The organic layer is dried and the solvent EPO <DP n="40"/>was removed under reduced pressure. The crude residue obtained is purified via column chromatography by eluting with petroleum ether: EtOAc to afford 1.9 g (53 percent) of the title compound as a pale yellow solid. LC/MS: (ES+): 180.1.
Reference: [1] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 255 - 264
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] European Journal of Organic Chemistry, 2009, # 27, p. 4655 - 4665
[4] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 5, p. 1125 - 1135
[5] Polyhedron, 2013, vol. 50, # 1, p. 101 - 111
[6] Patent: WO2007/23186, 2007, A1, . Location in patent: Page/Page column 38-39
[7] ChemMedChem, 2013, vol. 8, # 6, p. 946 - 955
[8] Journal of the Chemical Society, 1948, p. 777,781
[9] Patent: WO2011/60207, 2011, A1, . Location in patent: Page/Page column 48
[10] Patent: US2011/237584, 2011, A1, . Location in patent: Page/Page column 127
  • 3
  • [ 87885-47-0 ]
  • [ 34117-90-3 ]
  • [ 2213-63-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 4
  • [ 67-56-1 ]
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  • [ 34117-90-3 ]
  • [ 57315-34-1 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 5
  • [ 2213-63-0 ]
  • [ 64-17-5 ]
  • [ 34117-90-3 ]
  • [ 57315-33-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 6
  • [ 15804-19-0 ]
  • [ 2213-63-0 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With trichlorophosphate In N,N-dimethyl-formamide at 50℃; for 4 h;
Stage #2: With ammonia In waterCooling with ice
General procerure: A mixture of quinoxalin-2,3(1H,4H)-dione (1) [16] or compound 2 (40 mmol) and phosphours oxychloride (100 mmol) in dimethyl foramide (20 mL) was stirred at 50 °C for 4 h. The reaction mixture was added portion wise to ice/water and neutralized with ammonia solution 30percent. The formed precipitate was filtered off and purified on column chromatography by using petroleum ether (60-80): ethyl acetate (9:1) as an eluent.
80% for 5 h; Reflux A solution of compound 7 (30.84mmol, 5.0g) in phosphorus oxychloride (30mL) was reacted under refluxing condition for 5h, then the reaction was totally quenched by slowly pouring into cooled ammonia solution. The mixture was extracted with ethyl acetate (2×50mL), the combined organic phase was washed with brine (30mL) and dried over anhydrous MgSO4. After evaporated in vacuo, the crude residue was purified by silica gel flash chromatography (PE/EtOAc=10:1, v:v) to give 4.9g of corresponding product with 80percent yield. M.p. 149–150°C; ESI-MS m/z: 199.8 [M+H]+.
Reference: [1] Tetrahedron, 2008, vol. 64, # 22, p. 5410 - 5415
[2] ChemMedChem, 2012, vol. 7, # 5, p. 823 - 835
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 327 - 340
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 10, p. 936 - 940
[5] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[6] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 4, p. 771 - 777
[7] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1110 - 1112
[8] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 311 - 325
[9] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2260 - 2266
[10] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3689 - 3695
[11] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[12] Heterocycles, 2006, vol. 68, # 9, p. 1973 - 1979
[13] Journal of the Chemical Society, 1955, p. 1804,1806
[14] Patent: US2495202, 1945, ,
[15] Nippon Kagaku Zasshi, 1959, vol. 80, p. 945[16] Chem.Abstr., 1961, p. 4514
[17] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 1, p. 45 - 51
[18] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 12, p. 1371 - 1373
[19] Molecules, 2004, vol. 9, # 4, p. 223 - 231
[20] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5540 - 5548
[21] Heterocycles, 2012, vol. 86, # 2, p. 1583 - 1590
[22] Patent: CN103304584, 2016, B, . Location in patent: Paragraph 0017; 0018; 0025
[23] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 174 - 181
[24] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 117 - 134
[25] Patent: CN104529915, 2018, B, . Location in patent: Paragraph 0105; 0108; 0109
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YieldReaction ConditionsOperation in experiment
98% at 79 - 100℃; for 1 h; General procedure: N,N-Dimethylformamide (0.5 mg, 0.0673 mmol) was added dropwise to a slurry of 2,3-dihydroxyquinoxaline (2.0 g,12.3 mmol) and thionyl chloride (2.92 g, 24.6 mmol) in1-chlorobutane (20 mL). The mixture was refluxed for 1h.Then cooled to ambient temperature, the obtained needles were filtered, washed with ethyl ether, and dried.2,3-Dichloroquinoxaline (2a): white needles, yield 98percent; mp100–102 °C(lit. 16 m.p. 100–102 °C); FT-IR (KBr, cm-1):3049, 1618, 1562,753; 1H NMR (350 MHz, CDCl3): δ 8.07–8.02 (m, 2H, ArH), 7.85–7.80 (m, 2H, ArH); 13C NMR(CDCl3): 143.3, 140.9, 131.6, 127.8. Anal. Calcd. forC8H4Cl2N2: C, 48.28; H, 2.03; N, 14.07. Found: C, 47.52; H,1.89; N, 14.15.
96% With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 2 h; Reflux 31 mlof 1,2-dichloroethane in 3.5ml (48.1 mmol) of thionyl chloride and 3.0g (18.5mmol) of 2,3-dihydroxy quinoxaline in the slurry after the saline is slowlycatalytic amounts of dimethylformamide do. The reaction mixture was refluxedfor 2 hours. After the reaction was complete and then concentrated completelydissolved into the 35 ml of 1,2- dichloroethane it gives back again tocompletely concentrated. When the solid product thus obtained wasrecrystallized using acetonitrile and distilled water to obtain a solid whiteneedle-like crystals of 3.5 g (96percent yield).
95% With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide for 2 h; Reflux DMF (0.045 g, 0.00062 mol) was added dropwise to a slurry of 2,3-dihydroxyquinoxaline (2, 2.0 g,0.012 mol) and thionyl chloride (3.7 g, 0.031 mol) in 1,2-dichloroethane (20 mL). The resulting reactionmixture was heated to reflux for 2 h then concentrated to dryness. The residue was dissolved in1,2-dichloroethane (25 mL) and concentrated to dryness. The resulting solid was crystallized fromCH3CN/H2O, giving 2.3 g (95percent) of 3 as fine, off-white needles. m.p. 148–150 °C [55].
98% With thionyl chloride In N,N-dimethyl-formamide Comparative Example 2
Synthesis of 2,3-Dichloroquinoxaline
2,3-Dihydroxyquinoxaline (100.0 grams, 616.7 mmoles), thionyl chloride (350 mL) and dry DMF (5 mL) were added to a 500 mL flask.
The flask was connected to a condenser, which was connected to a dry column.
The mixture was gradually heated at reflux until the solid had completely dissolved, which took around 6 h.
Then excess thionyl chloride was removed under reduced pressure to yield 120.8 g (98percent) of crude 2,3-dichloroquinoxaline.
Recrystallizations from toluene gave 86.5 g (72percent) of white needles: mp 151-152° C.

Reference: [1] Revue Roumaine de Chimie, 2017, vol. 62, # 12, p. 903 - 906
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 149 - 153
[3] Molecules, 2012, vol. 17, # 4, p. 4533 - 4544
[4] Organometallics, 2014, vol. 33, # 7, p. 1617 - 1622
[5] Patent: KR2015/123096, 2015, A, . Location in patent: Paragraph 0111-0112; 0116-0118
[6] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 317 - 319
[7] Molecules, 2018, vol. 23, # 1,
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 7955 - 7970
[9] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[10] Synthetic Communications, 2005, vol. 35, # 15, p. 1983 - 1987
[11] Pesticide Science, 1995, vol. 43, # 4, p. 263 - 266
[12] Patent: US4291033, 1981, A,
[13] Patent: US2010/48857, 2010, A1,
[14] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[15] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7392 - 7401
[16] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
[17] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5303 - 5310
[18] Journal of Molecular Structure, 2017, vol. 1139, p. 238 - 246
[19] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
  • 8
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 110℃; for 5 h;
Stage #2: With trichlorophosphate In N,N-dimethyl-formamide; toluene at 110℃; for 1 h;
That 1 g O-phenylendiamine, 1.28 g oxalic acid and 3 g 200 - 300 mesh silica gel in the reaction bottle, adding 15 ml toluene, 110 °C lower reaction 5 hours, the reaction is finished, by adding 8.4 ml phosphorus oxychloride and 5 ml DMF, 110 °C continues reaction under 1 hour, the reaction is finished, adding 50 ml ice water quenching, adding 50 ml ethyl acetate, filtration, liquid, to continue to use the water layer is extracted with ethyl acetate, the combined ethyl acetate, washed with saturated sodium chloride, dried with anhydrous sodium sulfate, filtered, reduced-pressure drying to obtain white solid, yield 92percent
Reference: [1] Patent: CN108191778, 2018, A, . Location in patent: Paragraph 0019-0027
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Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 327 - 340
  • 10
  • [ 87885-47-0 ]
  • [ 34117-90-3 ]
  • [ 2213-63-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 11
  • [ 95-54-5 ]
  • [ 2213-63-0 ]
Reference: [1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 149 - 153
[3] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 1, p. 50 - 56
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5540 - 5548
[5] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[7] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
[8] Organometallics, 2014, vol. 33, # 7, p. 1617 - 1622
[9] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5303 - 5310
[10] Patent: KR2015/123096, 2015, A,
[11] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 311 - 325
[12] Patent: CN103304584, 2016, B,
[13] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3689 - 3695
[14] Molecules, 2018, vol. 23, # 1,
[15] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 117 - 134
[16] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
[17] Patent: CN104529915, 2018, B,
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  • [ 2213-63-0 ]
Reference: [1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Chemistry Letters, 1984, p. 323 - 326
[3] Chemistry Letters, 1984, p. 323 - 326
  • 13
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Reference: [1] Patent: US4358307, 1982, A,
  • 14
  • [ 91-19-0 ]
  • [ 2213-63-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 149 - 153
  • 15
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  • [ 2213-63-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1896, vol. 292, p. 246
  • 16
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  • [ 2213-63-0 ]
Reference: [1] Chemistry Letters, 1984, p. 323 - 326
  • 17
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  • [ 2213-63-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 18
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  • [ 2213-63-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1896, vol. 292, p. 246
  • 19
  • [ 15804-19-0 ]
  • [ 10026-13-8 ]
  • [ 2213-63-0 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 784
[2] Chemische Berichte, 1908, vol. 41, p. 800
  • 20
  • [ 20934-51-4 ]
  • [ 10026-13-8 ]
  • [ 2213-63-0 ]
Reference: [1] Journal of the Chemical Society, 1923, vol. 123, p. 1082
  • 21
  • [ 10026-13-8 ]
  • [ 65647-93-0 ]
  • [ 2213-63-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1896, vol. 292, p. 246
  • 22
  • [ 1196-57-2 ]
  • [ 10026-13-8 ]
  • [ 2213-63-0 ]
Reference: [1] Chemische Berichte, 1908, vol. 41, p. 800
  • 23
  • [ 2423-66-7 ]
  • [ 10025-87-3 ]
  • [ 2213-63-0 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 2816,2819
  • 24
  • [ 67-56-1 ]
  • [ 2213-63-0 ]
  • [ 32998-25-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 20℃; for 0.25 h;
Stage #2: at 20℃;
General procedure: A mixture of sodium (1 mmol, 0.023 g) and alcohol (3 mL) was stirred for 15 min at room temperature. Then 2,3-dichloroquinoxaline (1 mmol, 0.199 g) was added to the mixture until the complete consumption of the starting materials, monitored by TLC. After evaporation of the solvent, the resulting precipitate was washed with H2O; it did not require any further purification.
Reference: [1] Tetrahedron, 2016, vol. 72, # 41, p. 6536 - 6542
[2] Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1660 - 1673
[3] Tetrahedron, 2017, vol. 73, # 12, p. 1633 - 1639
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  • [ 124-41-4 ]
  • [ 32998-25-7 ]
YieldReaction ConditionsOperation in experiment
86% at 0 - 20℃; Reference Example 20 To a suspension of 2,3-dichloroquinoxaline (300 mg, 1.51 mmol) in methanol (15 mL) and N,N-dimethylformamide (1.0 mL) was added sodium methoxide (28percent in methanol, 309 mg, 1.66 mmol) dropwise at 0 0C. After being stirred for 2 hour at room temperature, the reaction mixture was concentrated in vacuo. The residue was diluted with chloroform and water. The organic layer was separated with phase separator and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane: ethyl acetate = 19: 1) to give 2-chloro-3-methoxyquinoxaline (the compound of Reference Example 20 listed in Table of Reference Example as described hereinafter) as a colorless powder (251 mg,percent).
Reference: [1] Patent: WO2010/30027, 2010, A1, . Location in patent: Page/Page column 60
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  • [ 32998-25-7 ]
Reference: [1] Molecules, 2012, vol. 17, # 7, p. 7737 - 7757
[2] Journal of the Chemical Society, 1955, p. 1804,1806
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 1035,1038
[4] Patent: US2005/148586, 2005, A1, . Location in patent: Page/Page column 19
[5] RSC Advances, 2016, vol. 6, # 87, p. 83901 - 83908
  • 27
  • [ 2213-63-0 ]
  • [ 32998-25-7 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[2] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
[3] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 11-12, p. 919 - 926
  • 28
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  • [ 70-55-3 ]
  • [ 4029-41-8 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 3, p. 340 - 344[2] Khimiya Geterotsiklicheskikh Soedinenii, 1994, # 3, p. 387 - 392
  • 29
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  • [ 77679-10-8 ]
  • [ 1062508-50-2 ]
  • [ 2537-48-6 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 2-3, p. 683 - 684
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