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CAS No. :49820-06-6 MDL No. :MFCD03103379
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SHOAYKZGNWFWSU-UHFFFAOYSA-N
M.W :175.18 Pubchem ID :2386161
Synonyms :

Safety of [ 49820-06-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 49820-06-6 ]

* 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.

  • Downstream synthetic route of [ 49820-06-6 ]

[ 49820-06-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 49820-06-6 ]
  • [ 90321-33-8 ]
YieldReaction ConditionsOperation in experiment
41.2% With dihydrogen peroxide; sodium hydroxide at 70℃; for 0.333333h; 3 Step 3 : synthesis of 2-amino-4,6-dimethylbenzoic acid 74-d H202 (123.7 g, 1200 mmol) was added to a mixture of intermediate 74-C (35.00 g,199.8 mmol) in NaOH solution (1225 mL, 0.33g/mL) at 70°C, over 5 minutes. Themixture was heated for another 15 minutes, then cooled to 15°C. Ice was added to the mixture. The resulting mixture was extracted with ethyl acetate (300 mL x 2). The pH of the solution was adjusted to 8 with addition of concentrated HC1 at 0°C and acidified to pH 6 with acetic acid. The mixture was extracted with ethyl acetate (300 mL x 2). The organic layers were combined, washed with brine, dried over Mg504 and filtered.The filtrate was concentrated to give intermediate 74-d (17 g, yield: 41.20%).
37% With dihydrogen peroxide; sodium hydroxide In water for 0.333333h; 89 To a heated (70° C. bath temperature) deep red solution of 4,6-dimethyl-1H-indole-2,3-dione (1.00 g, 5.71 mmol) in 33% aqueous sodium hydroxide (35 mL) was added 35% hydrogen peroxide (3.33 g, 34.3 mmol) over a period of 5 minutes. The reaction mixture was heated for another 15 min, then cooled to room temperature, and ice was added. The pH was adjusted to approximately 8 with concentrated HCl at 0° C. and acidified further to pH approximately 6 with glacial acetic acid. The solid precipitated was filtered, washed well with cold water, and dried under vacuum at 40° C. overnight to obtain 2-amino-4,6-dimethyl-benzoic acid as a pale brown solid. Yield: 0.35 g (37%)
37% With dihydrogen peroxide; sodium hydroxide at 70℃; for 0.333333h; 94 To a heated (70° C. bath temperature) deep red solution of 4,6-dimethyl-1H-indole-2,3-dione (1.00 g, 5.71 mmol) in 33% aqueous sodium hydroxide (35 mL) was added 35% hydrogen peroxide (3.33 g, 34.3 mmol) over a period of 5 minutes. The reaction mixture was heated for another 15 min, then cooled to room temperature, and ice was added. The pH was adjusted to approximately 8 with concentrated HCl at 0° C. and acidified further to pH approximately 6 with glacial acetic acid. The solid precipitated was filtered, washed well with cold water, and dried under vacuum at 40° C. overnight to obtain 2-amino-4,6-dimethyl-benzoic acid as a pale brown solid. Yield: 0.35 g (37%).
With sodium hydroxide; dihydrogen peroxide
11.0 g With sodium hydroxide; dihydrogen peroxide at 40℃; for 0.0833333h;

  • 2
  • [ 14812-64-7 ]
  • [ 49820-06-6 ]
  • [ 50314-40-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol for 24h; Heating;
  • 3
  • [ 79-37-8 ]
  • [ 49820-06-6 ]
  • [ 109082-06-6 ]
YieldReaction ConditionsOperation in experiment
77% With pyridine In dichloromethane for 12h; Heating;
  • 4
  • [ 623-73-4 ]
  • [ 49820-06-6 ]
  • 4-hydroxy-5,7-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • 3-hydroxy-5,7-dimethyl-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride In ethanol Heating;
  • 5
  • [ 266348-67-8 ]
  • [ 49820-06-6 ]
  • 4-benzoyl-5,7-dimethyl-1,4-dihydro-benzo[<i>d</i>][1,3]oxazin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 3% 2: 8% With N,N,N',N'-tetramethylguanidine In xylene for 6h; Heating;
  • 6
  • [ 266348-66-7 ]
  • [ 49820-06-6 ]
  • pentanoic acid 6,7-dimethyl-2-oxo-2,3-dihydro-1<i>H</i>-indol-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 1% 2: 19% With dmap In xylene for 7h; Heating;
  • 7
  • [ 266348-65-6 ]
  • [ 49820-06-6 ]
  • phenyl-acetic acid 4,6-dimethyl-2-oxo-2,3-dihydro-1<i>H</i>-indol-3-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 2% With dmap In xylene for 8h; Heating;
YieldReaction ConditionsOperation in experiment
With iodine; acetic acid
  • 9
  • [ 108-69-0 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 48 percent 2: 79 percent / AcOOH 3: 1 percent / DMAP / xylene / 7 h / Heating
Multi-step reaction with 3 steps 1: 40 percent 2: 79 percent / AcOOH 3: 3 percent / TMG / xylene / 6 h / Heating
Multi-step reaction with 3 steps 1: 82 percent 2: 96 percent / AcOOH 3: 2 percent / DMAP / xylene / 8 h / Heating
  • 10
  • [ 266348-55-4 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / AcOOH 2: 3 percent / TMG / xylene / 6 h / Heating
  • 11
  • [ 266348-54-3 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / AcOOH 2: 1 percent / DMAP / xylene / 7 h / Heating
  • 12
  • [ 266348-53-2 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / AcOOH 2: 2 percent / DMAP / xylene / 8 h / Heating
  • 13
  • [ 49820-06-6 ]
  • 6-methoxy-1,3,5,7-tetramethylfluorenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 11.0 g / 5percent H2O2, 40percent NaOH / 0.08 h / 40 °C 2: 46 percent 3: 1.) PCl5, 2.) AlCl3 4: 75 percent / H2SO4 5: 15 percent / HNO2
  • 14
  • [ 49820-06-6 ]
  • [ 107642-76-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 11.0 g / 5percent H2O2, 40percent NaOH / 0.08 h / 40 °C 2: 46 percent 3: 1.) PCl5, 2.) AlCl3 4: 75 percent / H2SO4
  • 15
  • [ 49820-06-6 ]
  • [ 107642-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 11.0 g / 5percent H2O2, 40percent NaOH / 0.08 h / 40 °C 2: 46 percent
  • 16
  • [ 49820-06-6 ]
  • [ 107642-75-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 11.0 g / 5percent H2O2, 40percent NaOH / 0.08 h / 40 °C 2: 46 percent 3: 1.) PCl5, 2.) AlCl3
  • 17
  • [ 49820-06-6 ]
  • [ 109082-15-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / pyridine / CH2Cl2 / 12 h / Heating 2: 0.5 h / Heating
  • 18
  • [ 99-12-7 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SnCl2; concentrated HCl; ethanol 2: hydroxylamine hydrochloride; sodium sulfate; aqueous hydrochloric acid / Erwaermen des Reaktionsprodukts mit wss.Schwefelsaeure
  • 19
  • [ 49820-06-6 ]
  • [ 49820-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: KOH / ethanol / 24 h / Heating 2: Cu chromite / 300 °C
  • 20
  • [ 108-69-0 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
R.4 4,6-Dimethylisatin Reference Example 4 4,6-Dimethylisatin This compound was prepared by the same method as that described in reference example 1, using 3,5-dimethylaniline in place of 3,5-dicloroaniline. 1H NMR (CDCl3, 270 MHz) δ 7.72 (brs, 1H), 6.69 (s, 1H), 6.51 (s, 1H), 2.53 (s, 3H), 2.36 (s, 3H).
Multi-step reaction with 2 steps 1: sodium sulfate; hydroxylamine hydrochloride; hydrogenchloride / water / 2.5 h / 45 - 75 °C 2: sulfuric acid / 0.5 h / 80 °C
Multi-step reaction with 2 steps 1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 2 h / 45 - 75 °C 2: sulfuric acid / 0.5 h / 80 °C
Multi-step reaction with 2 steps 1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 2.5 h / 20 - 75 °C 2: sulfuric acid / 0.5 h / 80 °C
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water 1.2: 0.5 h / 20 °C 1.3: 70 °C 2.1: sulfuric acid / water / 4 h / 80 °C

  • 21
  • concentrated H2 SO4 [ No CAS ]
  • tribromoacetaldehyde CBr3 CHO [ No CAS ]
  • [ 5470-11-1 ]
  • [ 108-69-0 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
With sodium sulfate In hydrogenchloride; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; ethyl acetate 41 Preparation of 4,6-dimethylisatin. Example 41 Preparation of 4,6-dimethylisatin. The procedure of Varma and Singh, Ind. J. Chem. 296:578-81 (1990), was adapted. To a solution of tribromoacetaldehyde CBr3 CHO (6.80 g, 24 mmol, Aldrich) in water (60 mL) and 1N HCl (2 mL) was added successively sodium sulfate (6.20 g, 43 mmol), a solution of 3,5-dimethylaniline (2.54 g, 21 mmol) in 1N HCl (40 mL), and a solution of hydroxyamine hydrochloride (5.50 g, 79 mmol) in water (25 mL). The mixture was heated to vigorous boiling and kept boiling for 10 min then cooled in ice bath to room temperature. It was filtered, washed by water, dried to leave pale yellow solid. The solid was added portionwise into concentrated H2 SO4 (50 mL) kept at 50° C. After the addition, the solution was heated to 80° C. for 15 min. It was cooled to room temperature, and added into ice water (450 mL). After standing for 0.5 h, it was filtered and washed with water and dried to leave a yellow solid. The solid was boiled with ethyl acetate (180 mL), filtered and cooled to room temperature. The crystalline solid was collected and dried to give the title compound (752 mg, 20%) containing a 2% impurity by NMR. Recrystallization from DMSO/H2 O afforded pure title compound as needles: mp 220°-2° C. IR (KBr, cm-1) 3439, 3211, 1762, 1729, 1628. 1 H NMR (DMSO-d6): δ2.821 (s, 3H); 2.380 (s, 3H); 6.517 (s, 1H); 6.673 (s, 1H); 10.931 (s, 1H). LRMS: calcd for C10 H9 NO2 m/z: 175; found: 175. Purity: >97.4% by HPLC.
  • 22
  • [ 49820-06-6 ]
  • [ 177944-75-1 ]
YieldReaction ConditionsOperation in experiment
With KNO3 In potassium hydroxide; concentrated H2 SO4 42 Synthesis of 4,6-dimethyl-5-nitroisatin. Example 42 Synthesis of 4,6-dimethyl-5-nitroisatin. The method of Cheesman, G. W. H.; J. Chem. Soc. 1170 (1962), was adapted. 4,6-Dimethylisatin (89 mg, 0.50 mmol) was dissolved in concentrated H2 SO4 (1.0 mL) at 0° C. for 30 min with stirring, then KNO3 (55 mg, 0.55 mmol, Baker) was added to this solution. The mixture was stirred at 25° C. for 24 h. It was then poured into ice water (5 g). The resulting precipitate was collected by filtration. The precipitate was dissolved in 1N KOH (5 mL) and the small amount of solid was removed by filtration, then the filtrate was acidified to pH 2 with 4N HCl (~1 mL) to give a yellow precipitate. The solid was collected by filtration and was washed with water (2*1 mL), then it was dried in the air at 50° C. for 4 h affording pure (by NMR) title compound (85 mg, 77%) as a yellow powder. Crystallization from acetone/water gave crystals. Mp 278°-80° C. (dec.). IR (KBr, cm-1): 3452, 3225, 2931, 1780, 1742, 1635, 1608, 1535. 1 H NMR (DMSO-d6): δ 11.357 (s, 1H), 6.771 (s, 1H), 2.389 (s, 3H), 2.305 (s, 3H). Purity >97.5% by HPLC.
  • 23
  • [ 49820-06-6 ]
  • [ 147494-08-4 ]
YieldReaction ConditionsOperation in experiment
31% In acetic acid 7.c c. c. 5,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione To a stirred warm (60° C.) solution of 4,6-dimethyl-1H-indole-2,3-dione (2.0 g, 11.4 mM) in acetic acid (20 mL) was added in small portions chromium trioxide (6.6 g, 66 mM) while maintaining the temperature of the reaction mixture at 65°-70° C. The reaction mixture was then heated at 80° C. for one hour, cooled, poured into water (150 mL) and filtered to obtain the the title compound (0.67 g, 31%) as a light yellow solid; MS(CI): 192 (M+H).
  • 24
  • [ 49820-06-6 ]
  • [ 67-64-1 ]
  • [ 1089663-46-6 ]
YieldReaction ConditionsOperation in experiment
With N-(2-thiophenesulfonyl)-L-prolinamide trifluoroacetate; water at 20℃; for 40h; optical yield given as %ee; enantioselective reaction;
  • 25
  • [ 1445-69-8 ]
  • [ 49820-06-6 ]
  • [ 109-77-3 ]
  • [ 1334175-96-0 ]
YieldReaction ConditionsOperation in experiment
80% With nickel dichloride In PEG 600 at 100℃; for 2.5h; 4.2. General procedure for synthesis of pyrazolophthalazinyl spirooxindoles General procedure: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 °C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2×10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.
  • 26
  • [ 1421739-76-5 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
46% With sulfuric acid at 80℃; for 0.666667h; Cooling with ice; 5-Hexyl-2,3-dihydro-1H-indole-2,3-dione (9) General procedure: A round-bottom flask is charged with concentrated sulfuric acid (33 ml) and is magnetically stirred at 50 °C open to the atmosphere. To the acid was added 2-[(benzyloxy)imino]-N-(4-n-hexylphenyl) (11 g, 32.5 mmole) in portions over 30 minutes. On completion of the addition the mixture was heated at 80 °C for an additional 10 minutes then allowed to cool to room temperature. The dark viscous solution was subsequently added in portions with rapid stirring to ice (750 ml). The crude product was isolated by vacuum filtration, and the filter cake washed with water. The crude product was dried under vacuum to give 6.3 g (85 %) of an orange solid.
23% With sulfuric acid at 50 - 80℃; for 0.333333h; Cooling with ice;
  • 27
  • [ 49820-06-6 ]
  • [ 501-65-5 ]
  • [ 1424209-50-6 ]
YieldReaction ConditionsOperation in experiment
75% With silver(I) acetate; palladium diacetate In 1,4-dioxane; acetonitrile at 100℃; for 30h; Inert atmosphere;
  • 28
  • [ 49820-06-6 ]
  • [ 875241-52-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide; dihydrogen peroxide / water / 0.33 h 2.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 20 °C 2.2: 17 h / 20 °C
Multi-step reaction with 2 steps 1.1: dihydrogen peroxide; sodium hydroxide / 0.33 h / 70 °C 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / tetrahydrofuran / 0.5 h / 20 °C 2.2: 17 h / 20 °C
  • 29
  • [ 49820-06-6 ]
  • [ 1246250-87-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide; dihydrogen peroxide / water / 0.33 h 2.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 20 °C 2.2: 17 h / 20 °C 3.1: sodium hydrogensulfite; toluene-4-sulfonic acid / N,N-dimethyl acetamide / 2 h / 110 °C
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; sodium hydroxide / 0.33 h / 70 °C 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / tetrahydrofuran / 0.5 h / 20 °C 2.2: 17 h / 20 °C 3.1: toluene-4-sulfonic acid; sodium hydrogensulfite / N,N-dimethyl acetamide; dichloromethane; methanol / 2 h / 110 °C
  • 30
  • [ 35162-44-8 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
44% With sulfuric acid at 80℃; for 0.5h; 89 N-(3,5-Dimethyl-phenyl)-2-hydroxyimino-acetamide (13.7 g, 71.3 mmol) was added to concentrated sulfuric acid (70 mL) in a 250 mL flask. The reaction mixture was then heated at 80° C. for 30 minutes, then cooled to room temperature, and poured into ice-water (200 mL). The precipitated solid was filtered and washed with water (100 mL) and dried under vacuum to give 4,6-dimethyl-1H-indole-2,3-dione as an orange solid. Yield: 5.53 g (44%)
5.53 g With sulfuric acid at 80℃; for 0.5h; 94 N-(3,5-Dimethyl-phenyl)-2-hydroxyimino-acetamide (13.7 g, 71.3 mmol) was added to concentrated sulfuric acid (70 mL) in a 250 mL flask. The reaction mixture was then heated at 80° C. for 30 minutes, then cooled to room temperature, and poured into ice-water (200 mL). The precipitated solid was filtered and washed with water (100 mL) and dried under vacuum to give 4,6-dimethyl-1H-indole-2,3-dione as an orange solid. Yield: 5.53 g (44%).
3.25 g With sulfuric acid In water at 80℃; for 4h;
  • 31
  • [ 49820-06-6 ]
  • (S)-tert-butyl 3,4,6-trimethyl-2-oxo-3-(trifluoromethylthio)indoline-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / -40 - 20 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere 2.1: dmap / dichloromethane / 3 h / 25 °C / Schlenk technique; Inert atmosphere 3.1: palladium on activated charcoal; hydrogen / methanol / 20 °C / Schlenk technique; Inert atmosphere 4.1: Quinine / diethyl ether / 36 h / 35 °C / Inert atmosphere; Schlenk technique
  • 32
  • [ 49820-06-6 ]
  • C21H29NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / -40 - 20 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere 2.1: dmap / dichloromethane / 3 h / 25 °C / Schlenk technique; Inert atmosphere
  • 33
  • [ 49820-06-6 ]
  • tert-butyl 3,4,6-trimethyl-2-oxoindoline-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / -40 - 20 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere 2.1: dmap / dichloromethane / 3 h / 25 °C / Schlenk technique; Inert atmosphere 3.1: palladium on activated charcoal; hydrogen / methanol / 20 °C / Schlenk technique; Inert atmosphere
  • 34
  • [ 49820-06-6 ]
  • [ 75-16-1 ]
  • C11H13NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4,6-dimethyl-1H-indole-2,3-dione; methylmagnesium bromide In tetrahydrofuran at -40 - 20℃; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water Schlenk technique; Inert atmosphere;
  • 35
  • (E)-N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide [ No CAS ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
49.74% With sulfuric acid at 80℃; for 0.5h; 2 Step 2 : synthesis of 4,6-dimethylindoline-2,3-dione 74-c Intermediate 74-b (15.00 g, 78.04 mmol) was dissolved in concentrated sulfuric acid (75 ml). The mixture was stirred at 80°C for 30 minutes. Then the mixture was cooled to room temperature and poured into ice water. Intermediate 75-c was precipitated,filtered and washed with water (8.50 g, 49.74%).
  • 36
  • [ 49820-06-6 ]
  • 4-(5-(azetidin-1-yl)-2-(1-(5,7-dimethylquinazolin-4-yl)piperidin-2-yl)-pyrazolo[1,5-a]pyrimidin-7-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide; dihydrogen peroxide / 0.33 h / 70 °C 2: 5 h / 150 °C 3: trichlorophosphate; triethylamine / 3 h / 0 °C / Reflux 4: triethylamine; trifluoroacetic acid / 2-methoxy-ethanol / 16 h / 50 °C
  • 37
  • [ 131543-46-9 ]
  • [ 108-69-0 ]
  • [ 49820-06-6 ]
YieldReaction ConditionsOperation in experiment
44% With copper(II) choride dihydrate; caesium carbonate; trifluoroacetic acid In 2-methyltetrahydrofuran; water at 70℃; for 5h; Schlenk technique; Inert atmosphere;
  • 38
  • [ 626-35-7 ]
  • [ 49820-06-6 ]
  • ethyl (Z)-2-(4,6-dimethyl-2-oxoindolin-3-ylidene)-2-nitroacetate [ No CAS ]
  • ethyl (E)-2-(4,6-dimethyl-2-oxoindolin-3-ylidene)-2-nitroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.667 % de With dmap; titanium tetrachloride In tetrahydrofuran at 0 - 20℃; for 24h; Overall yield = 74 %; stereoselective reaction;
  • 39
  • [ 49820-06-6 ]
  • 2,3-diallyl-1-benzyl-4,6-dimethyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: indium; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: tin(ll) chloride; acetic acid; hydrogenchloride / water / 2 h / 80 °C / Inert atmosphere 4: tetrahydrofuran; diethyl ether / 3 h / 20 °C / Inert atmosphere
  • 40
  • [ 49820-06-6 ]
  • 9-benzyl-5,7-dimethyl-4,9-dihydro-1H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: indium; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: tin(ll) chloride; acetic acid; hydrogenchloride / water / 2 h / 80 °C / Inert atmosphere 4: tetrahydrofuran; diethyl ether / 3 h / 20 °C / Inert atmosphere 5: Grubbs catalyst first generation / dichloromethane / 20 °C / Inert atmosphere
  • 41
  • [ 49820-06-6 ]
  • 9-benzyl-2,4-dimethyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: indium; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: tin(ll) chloride; acetic acid; hydrogenchloride / water / 2 h / 80 °C / Inert atmosphere 4: tetrahydrofuran; diethyl ether / 3 h / 20 °C / Inert atmosphere 5: Grubbs catalyst first generation / dichloromethane / 20 °C / Inert atmosphere 6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 8 h / 20 °C / Inert atmosphere
  • 42
  • [ 49820-06-6 ]
  • 3-allyl-1-benzyl-4,6-dimethylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: indium; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: tin(ll) chloride; acetic acid; hydrogenchloride / water / 2 h / 80 °C / Inert atmosphere
  • 43
  • [ 49820-06-6 ]
  • C20H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: indium; sodium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 44
  • [ 49820-06-6 ]
  • [ 1306909-36-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 45
  • [ 49820-06-6 ]
  • [ 2687-12-9 ]
  • 1-[(R)-1-phenyl-2-propenyl]-4,6-dimethyl-2,3-indolinedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; benzyl ((11bS)-2,6-bis(3,5-di(tert-butyl)-4-methoxyphenyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphosphepin-4-yl)-L-prolinate; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester at 40℃; Sealed tube; enantioselective reaction;
  • 46
  • [ 49820-06-6 ]
  • 7,9-dimethyl-3-(methylthio)-5H-[1,2,4]triazino[5,6-b]-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / water / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 °C
  • 47
  • [ 49820-06-6 ]
  • C12H12N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / water / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C
  • 48
  • [ 49820-06-6 ]
  • 7,9-dimethyl-N-(6-(pyrrolidin-1-yl)hexyl)-5H-[1,2,4]-triazino[5,6-b]indol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / water / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 °C 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C 4: tetrahydrofuran / Reflux
  • 49
  • [ 49820-06-6 ]
  • [ 79-19-6 ]
  • 7,9-dimethyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium carbonate In water Reflux;
  • 50
  • [ 49820-06-6 ]
  • 1,3,7,9-tetramethylindolo[2,1-b]quinazoline-6,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With copper (I) iodide; Potassium bicarbonate In N,N-dimethyl-formamide at 90℃; for 24h;
Same Skeleton Products
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