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Product Details of [ 118-48-9 ]

CAS No. :118-48-9 MDL No. :MFCD00006700
Formula : C8H5NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :TXJUTRJFNRYTHH-UHFFFAOYSA-N
M.W : 163.13 Pubchem ID :8359
Synonyms :

Calculated chemistry of [ 118-48-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.1
TPSA : 63.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : 1.01
Log Po/w (SILICOS-IT) : 2.09
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) : -2.11
Solubility : 1.26 mg/ml ; 0.00775 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.9 mg/ml ; 0.0116 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.14
Solubility : 0.119 mg/ml ; 0.000731 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.62

Safety of [ 118-48-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P272-P280-P302+P352-P305+P351+P338-P321-P333+P313-P337+P313-P363-P501 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 118-48-9 ]

* 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 [ 118-48-9 ]
  • Downstream synthetic route of [ 118-48-9 ]

[ 118-48-9 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 118-48-9 ]
  • [ 4743-17-3 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2689 - 2695
  • 2
  • [ 118-48-9 ]
  • [ 20198-19-0 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 13, p. 2933 - 2935
  • 3
  • [ 118-48-9 ]
  • [ 7726-95-6 ]
  • [ 4692-98-2 ]
YieldReaction ConditionsOperation in experiment
85% at 50℃; for 2 h; Bromine (35 mL, 660 mmol) was added dropwise to a suspension of isatoicanhydride (100 g, 610 mmol) in 1.6 L water at 50 °C. This temperature was maintained for an additional 2 hours. After cooling the solution to room temperature, the solid was filtered and washed twice with water and twice with acetone, yielding 125.6 g (85percent) 6-hromo-lH-benzo[d][l,3]oxazine-2,4-dione as a pink solid.
Reference: [1] Patent: WO2006/28904, 2006, A1, . Location in patent: Page/Page column 169
  • 4
  • [ 118-48-9 ]
  • [ 4692-98-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 2, p. 253 - 260
[2] MedChemComm, 2016, vol. 7, # 10, p. 1957 - 1965
[3] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2> 33, p. 36
  • 5
  • [ 118-48-9 ]
  • [ 4693-02-1 ]
YieldReaction ConditionsOperation in experiment
97.9% at 0 - 10℃; for 2 h; 250mL three-necked flask was added concentrated sulfuric acid (100mL), was added slowly with mechanical stirring at 0-10 ° C when isatoic anhydride 1 (30.0g, 0.18mol), after stirring and dissolving the dropwise addition of 65percent concentrated nitric acid (21.4g, 0.22 mol), maintaining the temperature at 0-10 ° C, 1h addition was complete, the reaction was continued and held for 1h, stopped stirring, the reaction mixture was slowly poured into 300mL ice-water mixture, stirred for 20min, fully precipitated solid was filtered, washed with water, dried after obtained 5-nitro isatoic anhydride 2 (37.5g, yield: 97.9percent).
Reference: [1] Patent: CN103613549, 2016, B, . Location in patent: Paragraph 0033-0035
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 23, p. 8032 - 8042
[3] Chemical Communications, 2013, vol. 49, # 2, p. 190 - 192
[4] Synthetic Communications, 2011, vol. 41, # 22, p. 3265 - 3279
[5] Journal fuer Praktische Chemie (Leipzig), 1884, vol. <2> 30, p. 474
[6] Tetrahedron, 1999, vol. 55, # 34, p. 10447 - 10466
[7] Patent: US2014/121414, 2014, A1, . Location in patent: Paragraph 0044
  • 6
  • [ 118-48-9 ]
  • [ 95-53-4 ]
  • [ 4943-85-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 108, p. 63039 - 63047
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 12, p. 2389 - 2391
[3] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2> 63, p. 244[4] Journal fuer Praktische Chemie (Leipzig), 1902, vol. <2> 65, p. 533
[5] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 531 - 535
[6] Tetrahedron Letters, 2008, vol. 49, # 41, p. 5840 - 5842
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 277 - 289
[8] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4736 - 4742
  • 7
  • [ 118-48-9 ]
  • [ 3820-67-5 ]
Reference: [1] Synthesis, 1980, vol. No. 1, p. 54 - 55
  • 8
  • [ 118-48-9 ]
  • [ 28797-48-0 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 8, p. 1820 - 1844
  • 9
  • [ 118-48-9 ]
  • [ 885-70-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 8, p. 1820 - 1844
  • 10
  • [ 118-48-9 ]
  • [ 593-51-1 ]
  • [ 4141-08-6 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In N,N-dimethyl-formamide at 40 - 120℃; for 3 h; General procedure: Isatoic anhydride derivatives were dissolved in dry DMF (30 mL) and treated with the corresponding amine (5 equiv) or a mixture of the amine hydrochloride (5 equiv) and triethylamine (5 equiv). The mixture was heated to 40–120 °C (depending on the amine) for 3–6 h. For workup, the mixture was poured into water (100 mL) and the product was extracted with EtOAc (5 × 100 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4and evaporated to dryness. The crude product was purified by column chromatography to obtain the benzamide derivatives.
86%
Stage #1: With triethylamine In ethanol at 20℃; for 0.0833333 h;
Stage #2: for 2 h; Inert atmosphere; Reflux
Methylamine hydrochloride (3.10 g, 46.0 mmol), ethanol (50 mL) and triethylamine (6.41 mL, 46.0 mmol) were stirred at room temperature for five minutes then isatoic anhydride (5.00 g, 30.7 mmol) was added. The mixture was heated at reflux for two hours under nitrogen and then allowed to cool to ambient temperature. The resulting mixture was concentrated, and the residue suspended in water (300 mL). The aqueous mixture was extracted with ethyl acetate (3x200 mL) then the combined ethyl acetate phases were washed with brine, dried (sodium sulphate) and evaporated. Chromatography (40 g silica cartridge, 0-80percent ethyl acetate in petroleum benzine 40-60 °C) gave the title compound (12) (3.97 g, 86percent yield) as a pale pink solid; 1H NMR (400 MHz, CDCI3) ? 7.29 (dd, J = 7.9, 1.5 Hz, 1H), 7.19 (ddd, J = 8.4, 7.2, 1.5 Hz, 1H), 6.67 (dd, J = 8.2, 1.1 Hz, 1H), 6.63 (ddd, J = 8.2, 7.3, 1.2 Hz, 1H), 6.11 (s, 1H), 5.46 (s, 2H), 2.95 (d, J = 4.8 Hz, 3H); 13C NMR (101 MHz, CDCI3) ? 170.14, 148.61 , 132.22, 127.23, 117.34, 116.68, 116.38, 26.56. LCMS: rt 2.61 min, m/z 120.2 [M-NHMe]+.
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2280 - 2292
[2] Patent: WO2013/75167, 2013, A1, . Location in patent: Page/Page column 29
  • 11
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  • [ 74-89-5 ]
  • [ 4141-08-6 ]
YieldReaction ConditionsOperation in experiment
99% for 2.5 h; Isatoic anhydride (25 g, 150 mmol) was combined with water (150 mL). Methylamine in THF (2.0 M, 150 mL) was added to the isatoic anhydride solution over thirty minutes. The mixture was stirred for 2 hours and then extracted with ethyl acetate. The organic layer was washed with water, then brine and dried over MgSO4, filtered and concentrated to yield an off-white powder (24 g, 99percent). 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 1H), 7.22 (m, 1H), 6.67 (m, 2H), 6.06 (br s, 1H), 5.52 (br s, 2H), 2.99 (d, 3H, J = 4.8 Hz).
97% for 0.333333 h; Example 3: Synthesis of Compound XIII-1; Step 1: Preparation of 2-Amino-N-meth lbenzamide (2); To a stirred suspension of Isatoic anhydride (1, 10 g, 61.3 mmol) in 1 ,4-dioxane ( 100 mL), methyl amine gas was passed for 20 min. The progress of the reaction was monitored by thin layerchromatography (TLC), and complete conversion of compound 1 to compound 2 was observed. The reaction mixture was then Filtered through Filter paper; and the solvent was evaporated from the filtrate under reduced pressure to afford 2-Amino-N-methylbenzamide as a brown solid (2, 9 g, 97 percent). NMR (CDClj): δ 7.39-7.10 (m, 2H), 6.70-6.60 (m, 2H), 3.00 (s, 3H).
97.8% at 20℃; for 16 h; Intermediate C1 2-amjno- .yen.-rnethvfbenz3mide Isatoic anhydride (10 g, 81.3 mmoi) was suspended in tetrahydrofuran (200 mi) and treated dropwise with methyiamine in methanol (40 percent, 10 mL) with stirring. After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure to afford the product 2-amino-W-methylbenzamide (9 g, yield 97.8 percent). NMR (400 MHz, CDCi3) δ ppm 7.14-7.32 (m, 2H), 8.60-6.72 (m, 2H), 6.05 (br s, 1 H), 2.97 (d, 3H, J = 5.0 Hz).
92% at 20℃; for 1 h; To a suspension of 16.3 g (100 MMOL) of ISATOIC anhydride in 100mL of H2O is added portionwise 100mL of 2N methylamine-tetrahydrofuran solution (200 MMOL) at room temperature. The reaction mixture is stirred for 1 hour and then extracted with AcOEt. The organic layer is washed with H20 and brine, dried over NA2SO4, and concentrated uhder reduced pressure to give 13.79 g of desired product, 2-amino-N-methyl-benzamide (92 MMOL, 92percent) as colorless solid. NMR (400MHZ, CD3, 5) : 2.97 (d, 3H, J = 4.52 Hz), 5.49 (bs, 1H), 6.07 (bs, 1H), 6.64 (ddd, 1H, J = 8.04, 7.56, 1.0 Hz), 6.68 (dd, 1H, J = 8.32, 1.0 HZ), 7.20 (ddd, 1H, J = 8.32, 7.56, 1.52 Hz), 7.29 (dd, 1H, J = 8.04, 1.52 Hz).
91.5% at 20℃; 10216] To a solution of benzoxazine ketone 16.30 g (0.1 mol) in 150 mE acetonitrile was slowly dropwise added 40percent methylamine aqueous solution at room temperature until the solid disappeared, about 80 ml methylamine aqueous solution was added. Then the reaction mixture was continued stirring at room temperature for another 0.5 hours and monitored by TEC. Afier the reaction was over, the mixture was concentrated under reduced pressure, the residual was filtered and washed with 50 ml of water and 50 ml of petroleum ether successively, then dried to give 13.73 g 2-amino-N-methyl- benzamide as white solid with yield of 91.5percent, m.p. 78-79° C. 10217] 3) The Preparation of 2-(2-chloroacetamido)-N- methylbenzamide
91.5% at 20℃; for 0.5 h; To a solution of benzoxazine ketone 16.30g (0.1mol) in 150 mL acetonitrile was slowly dropwise added 40percent methylamine aqueous solution at room temperature until the solid disappeared, about 80ml methylamine aqueous solution was added. Then the reaction mixture was continued stirring at room temperature for another 0.5 hours and monitored by TLC. After the reaction was over, the mixture was concentrated under reduced pressure, the residual was filtered and washed with 50ml of water and 50ml of petroleum ether successively, then dried to give 13.73g 2-amino-N-methylbenzamide as white solid with yield of 91.5percent, m.p. 78-79°C.
88% With acetic acid In ethyl acetate at 20℃; for 2 h; In a 250 mL reaction flask,16.3 g (0.1 mol) of isatoic anhydride was added100 mL of ethyl acetate,1mL glacial acetic acid,A solution of 15.5 g (0.15 mol) of a 40percent aqueous solution of methylamine was added dropwise at room temperature with stirring,Drop finished,Continue stirring 2h,Thin layer chromatography (TLC)Detection of raw materials disappeared,Ethyl acetate and water were distilled off,13.2 g of a white solid,Yield 88percent.
82% With triethylamine In tetrahydrofuran; water for 2.5 h; General procedure: A modified version of the reported procedure was employed.20 To a soln of isatoic anhydride (30 mmol) and Et3N (60 mmol) in H2O (30mL) was added a soln of the appropriate amine (60 mmol) in THF(30 mL) over 30 min. The mixture was stirred for 2 h and then extracted with EtOAc (3 × 30 mL). The combined organic layer was washed with H2O (3 × 30 mL) and brine (3 × 30 mL), then dried over MgSO4, filtered and concentrated to yield the desired amide.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 164 - 167
[2] Patent: WO2011/140338, 2011, A1, . Location in patent: Page/Page column 41
[3] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 61
[4] Patent: WO2004/80980, 2004, A1, . Location in patent: Page 110-111
[5] Patent: US2013/225585, 2013, A1, . Location in patent: Paragraph 0215; 0216
[6] Patent: EP2636669, 2013, A1, . Location in patent: Paragraph 0127; 0128
[7] Patent: CN105153113, 2016, B, . Location in patent: Paragraph 0025; 0026; 0027; 0028
[8] Synthetic Communications, 2012, vol. 42, # 1, p. 8 - 24
[9] Synthesis (Germany), 2013, vol. 45, # 21, p. 2998 - 3006
[10] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1281 - 1285
[11] Journal of Combinatorial Chemistry, 2010, vol. 12, # 5, p. 643 - 646
[12] RSC Advances, 2015, vol. 5, # 113, p. 93433 - 93437
[13] Tetrahedron, 2000, vol. 56, # 37, p. 7245 - 7253
[14] European Journal of Organic Chemistry, 2013, # 7, p. 1262 - 1270
[15] Journal fuer Praktische Chemie (Leipzig), 1887, vol. <2> 36, p. 145
[16] Journal fuer Praktische Chemie (Leipzig), 1887, vol. <2> 36, p. 145
[17] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 531 - 535
[18] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 103 - 105
[19] Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6245 - 6250
[20] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3019 - 3029
[21] Patent: WO2008/31548, 2008, A1, . Location in patent: Page/Page column 79-80
[22] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 660 - 663
[23] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 11, p. 3156 - 3157
[24] Tetrahedron, 2016, vol. 72, # 10, p. 1330 - 1336
[25] Organic Process Research and Development, 2017, vol. 21, # 5, p. 740 - 747
  • 12
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  • [ 4141-08-6 ]
YieldReaction ConditionsOperation in experiment
100% With methylamine In tetrahydrofuran; methanol REFERENCE EXAMPLE 12
2-Amino-N-methylbenzamide
Isatoic anhydride (10.0 g) was suspended in tetrahydrofuran (200 ml) and treated dropwise with 40percent solution of methylamine in methanol (10.0 ml) with stirring.
After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure to give the title compound (10.3 g, about 100percent).
Melting point: 78.0 to 79.0° C. (recrystallized from ethyl acetate-n-hexane).
IR (KBr): 3450, 3333, 1615, 1580, 1539 cm-1.
1H-NMR (CDCl3) δ: 2.97 (3H, d, J=5.0 Hz), 6.05 (1H, bs), 6.60-6.72 (2H, m), 7.14-7.32 (2H, m).
Reference: [1] Patent: US6407116, 2002, B1,
  • 13
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  • [ 74-89-5 ]
  • [ 4141-12-2 ]
  • [ 4141-08-6 ]
Reference: [1] Journal of Organic Chemistry, 1953, vol. 18, p. 1427,1433, 1437
  • 14
  • [ 118-48-9 ]
  • [ 56287-74-2 ]
Reference: [1] Patent: CN103613549, 2016, B,
  • 15
  • [ 118-48-9 ]
  • [ 26260-02-6 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 15, p. 4516 - 4520
  • 16
  • [ 118-48-9 ]
  • [ 35472-56-1 ]
Reference: [1] Organic Letters, 2018,
  • 17
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  • [ 124-40-3 ]
  • [ 6526-66-5 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1600 - 1604
  • 18
  • [ 118-48-9 ]
  • [ 32316-92-0 ]
  • [ 63449-68-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 22, p. 6114 - 6117
  • 19
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  • [ 77242-30-9 ]
Reference: [1] Patent: US2014/121414, 2014, A1,
  • 20
  • [ 118-48-9 ]
  • [ 64241-01-6 ]
YieldReaction ConditionsOperation in experiment
86.6% With methanol In methanol for 6 h; Heating / reflux EXAMPLE 386B methyl 2-amino-6-hydroxybenzoate [0691] A mixture of Example 386A (1.0 g, 5.6 mmol) and methanol (40 mL) was heated to reflux for 6 hours, concentrated, and purified on a silica gel column eluting with 30percent ethyl acetate in hexanes to provide the desired product, 0.81 g, 86.6percent. 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 5.95 (d, 1H), 6.20 (d, 1H), 6.34 (s, 214), 7.02 (t, 1H), 10.88 (s, 1H); MS (DCI/NH3): m/e 168 (M+H)+.
Reference: [1] Patent: US2004/167128, 2004, A1, . Location in patent: Page 76
  • 21
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  • [ 1439934-41-4 ]
Reference: [1] Patent: WO2013/75167, 2013, A1,
[2] RSC Advances, 2015, vol. 5, # 113, p. 93433 - 93437
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