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[ CAS No. 1885-29-6 ] {[proInfo.proName]}

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Product Details of [ 1885-29-6 ]

CAS No. :1885-29-6 MDL No. :MFCD00007631
Formula : C7H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :HLCPWBZNUKCSBN-UHFFFAOYSA-N
M.W :118.14 Pubchem ID :72913
Synonyms :

Calculated chemistry of [ 1885-29-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.56
TPSA : 49.81 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.15
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 1.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.95
Solubility : 1.33 mg/ml ; 0.0113 mol/l
Class : Very soluble
Log S (Ali) : -2.05
Solubility : 1.05 mg/ml ; 0.00891 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.0 mg/ml ; 0.00847 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 1885-29-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P272-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P333+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:3439
Hazard Statements:H301+H311+H331-H315-H319-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1885-29-6 ]

* 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 [ 1885-29-6 ]
  • Downstream synthetic route of [ 1885-29-6 ]

[ 1885-29-6 ] Synthesis Path-Upstream   1~43

  • 1
  • [ 67-64-1 ]
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  • [ 6628-04-2 ]
  • [ 77726-78-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 3, p. 533 - 542
  • 2
  • [ 67-64-1 ]
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  • [ 6628-04-2 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1993, vol. 26, # 9-10, p. 769 - 772
  • 3
  • [ 77287-34-4 ]
  • [ 1885-29-6 ]
  • [ 15018-66-3 ]
YieldReaction ConditionsOperation in experiment
72% at 170℃; for 0.5 h; Microwave irradiation; Sealed vial General procedure: Method A: Benzonitriles were suspended in formamide (40 equiv) and InCl3 (1 equiv), or not, in a sealed vial and were irradiated at 400 W under microwaves. The residue was cooled to room temperature, filtrated, washed with water and dried.
Reference: [1] Tetrahedron, 2011, vol. 67, # 26, p. 4852 - 4857
  • 4
  • [ 74-90-8 ]
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  • [ 15018-66-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2227 - 2238
  • 5
  • [ 122-51-0 ]
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  • [ 15018-66-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 4, p. 913 - 916
  • 6
  • [ 4637-24-5 ]
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  • [ 15018-66-3 ]
Reference: [1] Patent: KR2016/21163, 2016, A, . Location in patent: Paragraph 0680; 0682
  • 7
  • [ 3473-63-0 ]
  • [ 1885-29-6 ]
  • [ 15018-66-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 421 - 425
  • 8
  • [ 463-52-5 ]
  • [ 1885-29-6 ]
  • [ 15018-66-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 20, p. 6409 - 6422
  • 9
  • [ 1885-29-6 ]
  • [ 15018-66-3 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 26, p. 4852 - 4857
  • 10
  • [ 127099-85-8 ]
  • [ 1885-29-6 ]
  • [ 1899-48-5 ]
YieldReaction ConditionsOperation in experiment
21% With hydrogenchloride In water for 2 h; Reflux A mixture of 10.0 g (84.6 mmol) 2-aminobenzonitrile 39 and 7.12 g (84.6 mmol) cyanoguanidine 40 in 42 ml of 2N aqueous HCl were heated to reflux for 2 h. Subsequently, 320 ml of dest. water and 53 ml of 2 N aqueous NaOH were added to the yellow solution. To remove unreacted starting material the reaction mixture was treated with charcoal and filtered through a short column filled with Celite. After cooling to 4 °C the product precipitates in form of colorless needles which were filtered off and recrystallized from water to yield 2.90 g (21 percent) of 2,4-diaminoquinazoline 19. Mp.: 154-155 °C (lit.: 255 - 257 °C [12]). 1H-NMR(250 MHz, DMSO-d6): / ppm = 7.94 (dd,J =8.2 Hz,J =1.1 Hz, 1H, Ar-H); 7.47 (ddd,J =8.3 Hz,J =6.8 Hz,J =1.2 Hz, 1H, Ar-H); 7.25 (br, 2H, NH2); 7.18 (dd,J =8.4 Hz,J =0.8 Hz, 1H, Ar-H), 6.99 (ddd,J =8.3 Hz,J =6.8 Hz,J =1.2 Hz, 1H, Ar-H); 5.98 (s, 2H, NH2).13C-NMR(75.4 MHz, DMSO-d6): / ppm = 162.4, 160.7, 152.4, 132.3, 124.1, 123.5, 119.7, 110.3. IR: ν = 3505 (s), 3389 (s), 3172 (s), 3083 (m), 2827 (w), 2744 (w), 2669 (w), 2272 (w), 1952 (w), 1690 (s), 1658 (s), 1633 (s), 1574 (s), 1512(s), 1482 (s), 1418 (s), 1380 (s), 1341 (m), 1286 (s), 1253 (w), 1184 (w), 1157 (m), 1131 (w), 1080 (m), 1029 (m), 993 (m), 940 (w), 928(w), 889 (m), 856 (m), 798 (m), 753 (s), 678 (m), 590 (m). Anal.calcd. for C8H8N4(160.18): C 59.99; H 5.03; N 34.98; found: C 59.94; H 5.08; N 35.13.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5576 - 5580
  • 11
  • [ 593-85-1 ]
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Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 502 - 507
  • 12
  • [ 127099-85-8 ]
  • [ 1885-29-6 ]
  • [ 1899-48-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 434 - 444
[2] DRP/DRBP Org.Chem.,
  • 13
  • [ 420-04-2 ]
  • [ 1885-29-6 ]
  • [ 1899-48-5 ]
Reference: [1] DRP/DRBP Org.Chem.,
  • 14
  • [ 1885-29-6 ]
  • [ 29874-83-7 ]
Reference: [1] Patent: KR2016/28737, 2016, A,
[2] Patent: KR2015/144120, 2015, A,
[3] Patent: KR2015/145463, 2015, A,
[4] Patent: KR2018/23511, 2018, A,
[5] Patent: KR2015/144121, 2015, A,
[6] Patent: KR2017/77806, 2017, A,
  • 15
  • [ 100-58-3 ]
  • [ 1885-29-6 ]
  • [ 29874-83-7 ]
Reference: [1] Patent: KR2018/17580, 2018, A,
  • 16
  • [ 1885-29-6 ]
  • [ 61553-71-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8758 - 8780
  • 17
  • [ 1885-29-6 ]
  • [ 5081-87-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 5, p. 694 - 702
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[3] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[4] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[5] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[6] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[7] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[8] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[9] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[10] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
[11] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1553 - 1558
  • 18
  • [ 1885-29-6 ]
  • [ 4387-36-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With hydrogenchloride In water at 0 - 5℃; for 0.166667 h;
Stage #2: With 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dinitrite In water for 0.166667 h;
Stage #3: With potassium iodide In water at 20℃; for 0.25 h; Ionic liquid
General procedure: Aniline derivative (2 mmol) was dissolved in 1 ml of 37 percent HCl. The mixture was stirred at 0–5 C for 10 min, until the ammonium salt was formed and the aromatic amine disappeared. The progress of the reaction was monitored by TLC [eluent: n-hexane/ethyl acetate (80:20)]. Nitrite ionic liquid (1 mmol) was added to the aniline solution. The reaction mixture was ground mildly for 5–10 min, the diazonium salt was formed.Then, KI (5 mmol, 0.41 g) was added to the mixture and stirring continued for 5–20 min at room temperature (Table 1). The mixture was filtered and washed with distilled water (3 x 8 ml) and ethyl acetate (EtOAc, 15 ml). The residue was extracted with EtOAc (3 9 10 ml) and the combined organic layer was washed with 10 percent aqueous solution of Na2SO3 (15 ml) and then it was dried over anhydrous Na2SO4. The solvent was evaporated to afford aryl iodides.
53% With potassium iodide; camphorsulfonic acid; sodium nitrite In acetic acid at 20℃; for 12 h; General procedure: Potassium iodide (5.0 mmol) and   sodium nitrite (3.0 mmol) was added at room temperature to a solution of   aniline (2.5 mmol) and   camphorsulfonic acid (3.0 mmol) in   acetic acid (30 ml), and the mixture was stirred for 24 h. The evolution of N2 was immediately observed. The solvent was removed by a rotary evaporator after completion of the reaction (confirmed by β-naphthol test and TLC). The solid was washed with water and extracted with CH2Cl2. The resulting solution was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The pure product was then collected by column chromatography using   hexane/   dichloromethane as eluting solvents. Physical and 1H NMR data were identical to those of a commercially available sample of analytical purity.
Reference: [1] Research on Chemical Intermediates, 2013, vol. 41, # 6, p. 3999 - 4007
[2] Organic Letters, 2017, vol. 19, # 10, p. 2518 - 2521
[3] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[4] Journal of Chemical Sciences, 2013, vol. 125, # 1, p. 71 - 83
  • 19
  • [ 1885-29-6 ]
  • [ 39263-32-6 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With dihydrogen peroxide; ammonium bromide In water; acetic acid at 20℃; for 24 h;
Stage #2: With sodium hydroxide In water
A solution of 2-aminobenzonitrile (11.8g, 0.1 mol) in AcOH (120 ml) was treated with ammonium bromide (10.3 g, 0.105 mol) and hydrogen peroxide (10.2 ml, 35 percent in water, 0.105 mol). This mixture was stirred at room temperature for ca. 24 hours until LCMS analysis showed the reaction was complete. The mixture was concentrated to remove the AcOH, prior to stirring the residue with 30 percent aqueous NaOH solution until basic. The resulting solid was removed by filtration and washed with water before drying. This solid was then dissolved in an excess of DCM. The solution was concentrated until precipitation started and then allowed to stand until crystallisation was complete. The resulting solid was removed by filtration and washed with a little DCM. This gave the desired compound as an off white crystalline solid (19.2 g, 97 percent).1H NMR δ 7.61 (IH, d, J 2.5Hz), 7.43 (IH, dd, J 9, 2.5Hz), 6.75 (IH, d, J 9Hz), 6.28 (2H, br s); LC-MS rt 2.24
92% With N-Bromosuccinimide In dichloromethane at 0℃; for 2 h; To a stirred solution of 2-aminobenzonitrile (25 g, 210 mmol) in dichloromethane (500 mL) was added NBS (41.4 g, 230 mmol) portion wise and the mixture was stirred at 0 °C for 2 h. The reaction mixture was gradually warmed to room temperature and was quenched with sodium bicarbonate solution (200 mL). The organic layer was separated, washed with brine, dried over sodium sulfate andconcentrated under reduced pressure to afford 2-amino-S -bromobenzonitrile (38 g, 92percent yield) as a pale brown solid: ‘H NMR (400 MHz, DMSO-d6) 7,61 (d, J 2.5 Hz, 1H), 7.43 (dd,J= 9,2.5 Hz, 1H), 6.75 (d,J= 9Hz, 1H), 6.28 (bs, 2H).
92.6% With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; 1L in the reactor into a 2-aminobenzonitrile 35.1 g (297 mmol), N-bromosuccinimide 55.56 g (312 mmol) and 350 mL of dimethylformamide was stirred for 4 hours. Insert the distilled water, to remove the resulting solids by filtration and the reaction solution by column chromatography to give the intermediate 1-a 54.2 g (yield 92.6percent).
92.6% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4 h; Inert atmosphere 1L reactor while nitrogen to 2-amino-benzonitrile 35.1 g (297 mmol), 350 mL of dimethylformamide is stirred. Then put the N-bromo-succinimide 55.56 g (312 mmol) slowly to the reactor. After raising to room temperature, the mixture was stirred for 4 hours. When the reaction is completed, distilled water was added dropwise thereto at room temperature, brown crystals were filtered saenggimyeon The crystals were separated by column chromatography to obtain the compound 54.2 g (yield: 92.6percent) represented by [Intermediate 5-a].
92.6% With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; In a 1-L reactor, 2-aminobenzonitrile (35.1 g, 297 mmol), N-bromosuccinimide (55.56 g (312 mmol), and dimethylformamide (350 mL) were placed and stirred together for 4 hours. Distilled water was added before filtration of the reaction mixture. Purification by column chromatography afforded Intermediate 1-i (54.2 g): yield 92.6percent
89% With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.116667 h; General procedure: To a magnetic solution of aromatic compound (1 mmol)in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) wasadded and stirred at room temperature for the appropriatetime (Table 1). The reaction was monitored by TLC (eluent:n-hexane/ethyl acetate: 5/1). The reaction mixture was transferredinto a separatory funnel after filtration of OXBTEABand was extracted with water (15 mL) and dichloromethane(20 mL). The organic layer was dried over anhydrousNa2SO4, and the solvent was concentrated in a rotary evaporator.The crude product was purified by passing it over acolumn of silica gel using a mixture of n-hexane and ethylacetate as the eluent. In order to regenerate the reagent, whitesolid was treated with liquid bromine. All the product structureswere confirmed by comparison of melting point or 1HNMR spectra with ones reported in the literature [29a-29e].
83% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Step 1 : 2-Amino-5-bromobenzonitrile (P36a)To a solution of 2-aminobenzonitrile (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The mixture was stirred overnight at rt, then water (30 mL) was added and the mixture was extracted with Et20 (3 x 250 mL). The organic layer was washed with brine, dried over Na2S04, concentrated and purified by CC to give compound P36a (19 g, 83percent).
83% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Step 1: 2-Amino-5-bromobenzonitrile (P4a)To a solution of 2-aminobenzonitrile (14.9 g, 100 mmol) was added a solution of NBS (17.8 g,100 mmol) in DMF at ii. The mixture was stirred overnight at rt, then water (30 mL) was addedand the mixture was extracted with Et20 (3 x 250 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC to give compound P4a (19 g, 83percent).
83% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; Step 1 : 2-Amino-5-bromobenzonitrile (P4a) To a solution of 2-aminobenzonitrile (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The mixture was stirred overnight at rt, then water (30 mL) was added and the mixture was extracted with Et20 (3 x 250 mL). The organic layer was washed with brine, dried over Na2S04, concentrated and purified by CC to give compound P4a (19 g, 83percent).
70% With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 20℃; N-bromosuccinimide (17.8 g, 0.10 mol) was added in portions at room temperature to a stirred solution of anthranilonitrile (Aldrich, 11.8 g, 0.10 mol) in DMF (100 mL).After a mild exothermic reaction occurred, the red solution was stirred under nitrogen overnight. The reaction mixture was diluted with water (-100 mL) and CH2C12 (200 mL). The phases were separated. The organic phase was washed with [H20] (3X) and brine, dried [(NA2S04)] and concentrated in vacuo to give 21 g of red residue which was dissolved in ether (25 mL), and hexane was added to knock out 13.6 (70 percent yield, lst crop) g of red solid product: [MP] [95-97 C.] IR (diffuse reflectance) 3357,2219, 1633, 1560,1486, 1305,1257, 1180,1157, 889,866, 830,666, 656,641 [CRRI 1.] Anal. Calcd for [C7HSBRN2] : C, 42.67 ; H, 2.56 ; N, 14.22 ; Br, 40.55. Found: C, 42.75 ; H, 2.54 ; N, 14.25 ; Br, 40.34.
62% With N-Bromosuccinimide In dichloromethane at 0℃; for 2 h; N-Bromosuccinimide (12.5g, 0.07mol) was added in portions to a solution of anthranilonitrile (7.5g, 0.06mol) in DCM at O0C. The mixture was stirred at O0C for 2h and allowed to warm to ambient temperature. The precipitate formed was removed by filtration and the filtrate washed with saturated NaHCO3, brine and dried (MgSO4). Filtration and evaporation of solvent afforded the title compound (11.3g, 62percent). 1H NMR (CDCl3) 7.49 (IH, s), 7.40 (IH, d), 6.65 (IH, d), 4.39 (2H, br s).

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[8] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 187; 188
[9] Patent: KR2016/2328, 2016, A, . Location in patent: Paragraph 0401-0403
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[11] Patent: US2018/72753, 2018, A1, . Location in patent: Paragraph 0120-0121
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[13] Organic Letters, 2014, vol. 16, # 23, p. 6228 - 6231
[14] Patent: WO2012/139775, 2012, A1, . Location in patent: Page/Page column 63
[15] Patent: WO2013/178362, 2013, A1, . Location in patent: Page/Page column 94
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  • [ 114344-60-4 ]
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[2] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152
  • 21
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  • [ 68385-95-5 ]
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  • 23
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  • 24
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  • [ 3930-83-4 ]
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  • 25
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  • 26
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[2] Synthesis, 1985, # 6/7, p. 669 - 670
  • 27
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  • 28
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  • 29
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  • [ 68385-95-5 ]
YieldReaction ConditionsOperation in experiment
98% With bromine In acetic acid at 15 - 20℃; for 5 h; Bromine (3.52 g, 0.022 mol) was added dropwise to a magnetically stirred, cooled (ice-water bath) solution of 2-aminobenzonitrile 2 (1.18 g, 0.01 mol) in acetic acid (30 mL) at 15-20 °C over 10 min. The reaction mixture was stirred at room temperature for 5 h, then added to ice-water (100 mL), and the white precipitate was collected by filtration. The precipitate was washed thoroughly with water, and dried on Na2SO4 at room temperature to afford a white solid mass 7 (98percent), mp 155-156 °C (Lit,26 156 °C); Rf (30percent EtAcO/hexane) 0.37. 1H NMR (300 MHz, CDCl3): δ 7.73 (d, 4J=2.3 Hz, 1 H), 7.48 (d, 4J=2.3 Hz, 1 H), 4.90 (br s, 2 H) ppm. 13C NMR (75 MHz, CDCl3): δ 146.4, 139.6, 133.8, 115.8, 109.9, 108.4, 98.1 ppm. All data were identical to that reported in the literature.26
77% With N-Bromosuccinimide In acetonitrile at 80℃; for 3 h; A mixture of 2-aminobenzonitrile (5 g, 42.3 mmol) and NBS (16.57g, 93.1 mmol, 2.2 equiv) was refluxed in MeCN (80 mL) for 3 h. After cooling, the precipitate formed was filtered, washed with H2O (3 × 60 mL), and dried in a vacuum drying oven (desiccator cabinet). Recrystallization from propan-2-ol gave 1 as a brown solid; yield: 8.9 g (77percent); mp 158 °C (Lit.14 mp 156 °C). 1H NMR (200 MHz, CDCl3): δ = 4.91 (s, 2 H, NH2), 7.47 (d, J = 2.1Hz, 1 H, H-4), 7.71 (d, J = 2.1 Hz, 1 H, H-6). 13C NMR (50 MHz, CDCl3): δ = 97.9, 108.2, 109.7, 115.6, 133.6,139.4, 146.2.
Reference: [1] European Journal of Organic Chemistry, 2010, # 34, p. 6588 - 6599
[2] Tetrahedron, 2016, vol. 72, # 35, p. 5323 - 5330
[3] Archiv der Pharmazie, 2018, vol. 351, # 9,
[4] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 5, p. 738 - 744
[5] Synthesis (Germany), 2014, vol. 46, # 12, p. 1613 - 1620
[6] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3806 - 3817
[7] Journal of the American Chemical Society, 1903, vol. 25, p. 939
[8] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
[9] Patent: WO2017/120429, 2017, A1, . Location in patent: Page/Page column 304
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  • [ 39263-32-6 ]
  • [ 68385-95-5 ]
  • [ 114344-60-4 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085
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  • [ 39263-32-6 ]
  • [ 68385-95-5 ]
Reference: [1] Archiv der Pharmazie, 2018, vol. 351, # 9,
[2] Tetrahedron Letters, 2010, vol. 51, # 10, p. 1383 - 1385
  • 32
  • [ 1885-29-6 ]
  • [ 132664-45-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 11, p. 2919 - 2925
  • 33
  • [ 1885-29-6 ]
  • [ 132131-24-9 ]
YieldReaction ConditionsOperation in experiment
92.6% at 20℃; for 12 h; General procedure: Followed previous procedures: 1 a mixture of 2-aminobenzonitrile (0.02 mol) and ammonium iodide (0.02 mol) were dissolved in acetic acid (50 mL), and then 30percent aqueous hydrogen peroxide solution (0.13 mol) was slowly added at room temperature and stirred for 12 h. After reaction completion, the reaction solution was treated with aqueous sodium thiosulfate solution 40 mL (0.03 mol) and basified to about pH~8 by the addition of 20percent sodium hydroxide. The reaction mixture was stirred at room temperature for 0.5 h. The desired product, which was partially precipitated during this step, was isolated by vacuum filtration to afford A as silvery white flake solid (yield 92.6percent).
84.9% at 20℃; for 3 h; The 2.0g (16.9mmol) 2- aminobenzonitrile (Compound of Formula II) was dissolved in 20mL glacial acetic acid; was slowly added dropwise 2.8g (17.2 mmol) 10mL glacial acetic acid solution of iodine monochloride dropwise was completed, the reaction mixture was stirred 3H at room temperature; the reaction mixture was poured into 150mL ice water, Suction filtered, the filter cake was washed with water, dried with cyclohexane - toluene: Recrystallization (9 1, v / v), to give 2-amino-5-iodobenzonitrile (formula III Compound) (3.5g, molar yield of 84.9percent, HPLC purity 98.7percent),
48% With ammonium iodide; dihydrogen peroxide; acetic acid In water at 20℃; for 12 h; [612] Preparation 52: Synthesis of 2-amino-5-iodo-benzonitrile [613] [614] 2-Amino-benzonitrile (10g, 0.085mol) and ammonium iodide (13.5g, 0.094mol) were dissolved in acetic acid (200mL). 30percent aqueous hydrogen peroxide solution (5.3mL, 0.094mL) was slowly added at room temperature and stirred for 12 h. After completion of the reaction, the reaction solution was filtered through celite. The filtrate was treated with aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. The solid obtained using dichloromethane (10mL) and hexane (200mL) was filtered and dried under nitrogen gas to give the title compound (10g, Yield 48percent). [615] NMR: 1H-NMR(CDCl3) δ 7.64 (1H, d), 7.56 (1H, dd), 6.35 (1H, d), 4.44 (2H, br s) [616] Mass(EI) 245 (M++1) [617]
Reference: [1] Acta Crystallographica Section C: Crystal Structure Communications, 2007, vol. 63, # 7, p. o408-o410
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1584 - 1587
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4309 - 4313
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2637 - 2649
[5] Patent: CN103896889, 2016, B, . Location in patent: Paragraph 0041-0043
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 10, p. 959 - 964
[7] European Journal of Medicinal Chemistry, 1992, vol. 27, # 1, p. 7 - 18
[8] Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7522 - 7526
[9] Patent: WO2011/43568, 2011, A2, . Location in patent: Page/Page column 46
[10] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S539-S540
[11] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 83 - 84
[12] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6124 - 6128
[13] Patent: WO2010/61400, 2010, A1, . Location in patent: Page/Page column 14
[14] Patent: WO2011/39759, 2011, A1, . Location in patent: Page/Page column 13
  • 34
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  • [ 132131-24-9 ]
YieldReaction ConditionsOperation in experiment
73% at 20℃; for 18 h; N-iodosuccinimide (11.35 g, 50.4 mmol) was added in several portions at room temperature to a solution of anthranilonitrile (Aldrich, 5.87 g, 49.7 mmol) in DMF (80 mL) and stirred under N2 for 18 h. The reaction mixture was concentrated to [1/4] volume and diluted with [H20] (200 mL) and [CH2C12.] The phases were separated. The organic phase was washed with H2O, dried [(NA2SO4),] and concentrated in vacuo to give 14 g of dark liquid that was dissolved in hot ethanol and diluted with ca. 100 mL of hot H2O. The solution was cooled to room temperature overnight. The crystallized mixture was filtered and the pink mica-like sheets were washed with [H20] and dried in a vacuum oven at [40 C] to give 8. 85 g (73percent) of product; mp [76-78 C] : MS (EI) [INTO] (rel. intensity) 244 (M+, 99), 245 (12), 127 (9), 118 (9), 117 (72), 90 (75), 84 (11), 64 (14), 63 (42), 62 (13).
Reference: [1] Patent: WO2004/18461, 2004, A2, . Location in patent: Page 40-41
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  • [ 7790-99-0 ]
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  • [ 132131-24-9 ]
Reference: [1] Patent: US2011/263852, 2011, A1, . Location in patent: Page/Page column 11
  • 36
  • [ 1885-29-6 ]
  • [ 132131-24-9 ]
  • [ 114344-67-1 ]
Reference: [1] Synthetic Communications, 2008, vol. 38, # 22, p. 3894 - 3902
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  • [ 121554-10-7 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 4, p. 717 - 720
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 205 - 221
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Reference: [1] Synthetic Communications, 2000, vol. 30, # 20, p. 3669 - 3675
[2] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085
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Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 2, p. 146 - 149
  • 41
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  • [ 431046-20-7 ]
Reference: [1] Patent: WO2012/139775, 2012, A1,
[2] Patent: WO2013/178362, 2013, A1,
[3] Patent: WO2014/23367, 2014, A1,
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  • [ 1224887-10-8 ]
Reference: [1] Patent: WO2013/3575, 2013, A1,
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  • [ 1445251-22-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9556 - 9568
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