[ CAS No. 20780-72-7 ]

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2D
Chemical Structure| 20780-72-7
Chemical Structure| 20780-72-7
Structure of 20780-72-7

Quality Control of [ 20780-72-7 ]

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Product Details of [ 20780-72-7 ]

CAS No. :20780-72-7MDL No. :MFCD03618555
Formula :C8H4BrNO2Boiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :226.03Pubchem ID :-
Synonyms :

Computed Properties of [ 20780-72-7 ]

TPSA : 46.2 H-Bond Acceptor Count : 2
XLogP3 : 1.4 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 20780-72-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20780-72-7 ]

  • Upstream synthesis route of [ 20780-72-7 ]

[ 20780-72-7 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
83%
Stage #1: at 50 - 80℃; for 0.33 h;
Stage #2: at 0℃; for 1.00 h;
Example 59; Preparation of A33; Synthesis of 4-Bromoisatin (K-98) and 6-Bromoisatin (K-99); To a solution chloral hydride (50.0 g, 0.247 mol) in water (237mL) were successively added Na2SO4 (69.Og, 0.486mol), 3-bromoaniline (40.Og, 0.233mol) in a mixture of 37percent HCl (25ml, 0.302mol) and water (632ml) with vigorous stirring. After the addition was completed, the resulting reaction mixture was heated to reflux for 10 min, and allowed to cool to room temperature. The precipitate formed was collected by filtration, washed with water (3 x 100 ml) and dried in vacuo to yield the crude isonitrosoacetanilide. This product was added portion-wise to rapidly stirred concentrated H2SO4 (790ml) at a rate to keep the reaction temperature between 50 and 7O0C. The reaction mixture was heated to 80 0C for 20 min and allowed to cool to room temperature. The cooled mixture was poured into crushed ice (ca.3200g). The mixture was allowed to stand for Ih. The orange precipitate was collected by a filtration, washed with water and dried to yield a mixture of 4-bromoisatin (K-98) and 6-bromoisatin (K-99) (4Og, 83percent).
Reference: [1] Patent: WO2006/44415, 2006, A2. Location in patent: Page/Page column 118
[2] Synthetic Communications, 2010, vol. 40, # 21, p. 3125 - 3134
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 4, p. 935 - 946
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4641 - 4649
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 18 - 36
[6] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 4, p. 764 - 769
[7] Molecules, 2017, vol. 22, # 9,
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YieldReaction ConditionsOperation in experiment
51%
Stage #1: With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 20℃; for 0.08 h;
Stage #2: at 20 - 90℃; for 1.25 h;
Stage #3: With sulfuric acid In water at 50 - 65℃; for 0.50 h;
3-bromoaniline 10.00 g (58.13 mmol)Placed in a 1000 mL round bottom flask,Add 500mL of water,To the mixture was added 64.41 g (453.43 mmol) of anhydrous sodium sulfate,And hydroxylamine hydrochloride (13.33 g, 191.84 mmol)Then add 2mol / L hydrochloric acid solution 10mL,Stirred at room temperature for 5 min,Finally, 10.58 g (63.95 mmol) of chloral hydrate was added.The reaction mixture was stirred at room temperature for 15 min,And then heated under reflux at 90 ° C for 2 h.TLC detection of raw materials disappeared,Then cooled to room temperature,Filter,Vacuum drying,A pale yellow solid of 12.90 g was obtained. 40 mL of concentrated sulfuric acid was added to a 100 mL round bottom flask,12.90 g of a yellow solid was slowly added to concentrated sulfuric acid at 50 ° C,After the addition of the reaction at 65 ° C for 30 min.After completion of the reaction, the mixture was cooled to room temperature,The reaction mixture was then poured into an ice-water mixture,Stirring for 30min,Filter the red solid,Vacuum drying oven,Petroleum ether: ethyl acetate = 5: 1, 200 mesh silica gel column chromatography,4-bromoindole diketone 7.42 g, yield 51percent.
51%
Stage #1: With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 2.33 h;
Stage #2: at 50 - 65℃; for 0.50 h;
3-bromoaniline 10.00g (58.13mmol) was put into a 1000 ml round bottom flask. Add 500 ml water. Under stirring condition, add anhydrous sodium sulfate 64.41g (453.43mmol) and hydroxylamine hydrochloride 13.33g (191.84mmol), then add 2 mol/L hydrochloric acid solution 10 ml, stir at room temperature 5min, finally adding chloral hydrate 10.58g (63.95mmol). The reaction mixture stirring at the room temperature 15min, then 90 °C heating under reflux 2h. TLC detection raw material disappears, then cooling to room temperature, filtered, vacuum drying, to obtain light yellow solid 12.90g.
40 ml concentrated sulfuric acid was added into a 100 ml round-bottom flask. Under 50 °C, 12.90g yellow solid slowly added to the concentrated sulfuric acid. After completely adding, under 65 °C reaction 30min. After the reaction cooled to room temperature, then the reaction mixture is poured into ice-water mixture in the to, stirring 30min, filtered to get red solid, vacuum drying oven drying, petroleum ether: ethyl acetate=5: 1,200 mesh silica gel column chromatography purification, be 4-bromoisatin 7.42g, yield 51percent.
38.1% With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 0.08 h; General procedure: To a solution of 120mL water, chloral hydrate (8.93g, 0.054mol), anhydrous sodium sulfate (130g, 0.40mol), aniline or substituted aniline 5 (0.05mol), hydroxylammonium chloride (10.98g, 0.158mol) and concentrated hydrochloric acid (43mL) were added respectively. Subsequently, the resulting suspension was heated to 90°C for 5min and cooled to room temperature. After filtration and washing with water (2×20mL), the crude material was obtained. The crude was added in batches to a 250mL, three mouth flask filled with concentrated sulfuric acid (32.6mL) at the temperature of 65°C and then heated up to 80°C for 20min. The reaction solution was cooled to room temperature and poured onto 500g of ice water and stirred vigorously for 4h. Intermediates 6a–i were isolated by filtration, washing with water, and recrystallization from ethanol with yields from 25.7percent to 73.2percent.
Reference: [1] Patent: CN104370799, 2017, B. Location in patent: Paragraph 0024; 0026; 0027; 0028
[2] Patent: CN104387312, 2017, B. Location in patent: Paragraph 0023; 0024; 0025
[3] Chinese Chemical Letters, 2013, vol. 24, # 10, p. 929 - 933
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YieldReaction ConditionsOperation in experiment
87% With iodine pentoxide In dimethyl sulfoxide at 80℃; General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 18, p. 1747 - 1750
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YieldReaction ConditionsOperation in experiment
27% at 60 - 80℃; for 0.75 h; Sulfuric acid (1 L) was heated in a 3 L beaker on a hot plate to 60 °C and then removed. The dry isonitrosoacetanilide 2a-f was added in portion with stirring over 30 min so that the temperature did not exceed 65 °C. The mixture was then heated to 80 °C for 15 min, allowed to cool to 70 °C and cooled on ice. The solution was poured onto crushed ice (5 L) and left to stand for 1 h before filtering the orange-red precipitate. The product was washed by stirring with water (400 mL) and filtered to give a mixture of 3a-f and 4a-f. The crude product was dissolved in a solution of NaOH (20 g) in water (200 mL) at 60 °C, and then acidified with acetic acid (60 mL). After standing 0.5 h and cooling to 35 °C, the 4a-4f precipitate was filtered and washed with water (50 mL). The combined filtrate and washings were acidified with conc. HCL (60mL) and, after standing for 2 h at 5 °C, the 3a-f precipitate was filtered off and washed with water (50 mL). Yields: 3a: 27percent, 3b: 14percent, 3c : 29percent, 3d: 22percent, 3e: 33percent, 3f : 31percent, 4a: 56percent, 4b: 64percent, 4c: 53percent, 4d: 59percent, 4e: 49percent, 4f : 51percent.
Reference: [1] Patent: WO2005/41954, 2005, A1. Location in patent: Page/Page column 24; Figure 2A
[2] Journal of Organic Chemistry, 1956, vol. 21, p. 169
[3] Australian Journal of Chemistry, 1999, vol. 52, # 11, p. 1061 - 1069
[4] Patent: WO2005/80335, 2005, A1. Location in patent: Page/Page column 26; 35
[5] Synlett, 2016, vol. 27, # 10, p. 1516 - 1520
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YieldReaction ConditionsOperation in experiment
51% at 50 - 65℃; for 0.50 h; Take 40mL concentrated sulfuric acid was added to a 100mL round bottom flask,12.90 g of a yellow solid was slowly added to concentrated sulfuric acid at 50 ° C,After completely adding 65 reaction 30min. After the reaction was cooled to room temperature,The reaction mixture was then poured into an ice-water mixture, stirred for 30 min, and filtered with suction to give a red solid.Dried under vacuum oven, petroleum ether: ethyl acetate = 5: 1,200 mesh silica gel column chromatography,4 - Bromoindole dione7.42 g, yield 51percent.
Reference: [1] Patent: CN104402794, 2017, B. Location in patent: Paragraph 0030; 0032
[2] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 292 - 302
[4] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 370 - 378
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Reference: [1] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4641 - 4649
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 292 - 302
[4] Patent: CN104402794, 2017, B
[5] Molecules, 2017, vol. 22, # 9,
[6] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 370 - 378
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2891 - 2895
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6293 - 6297
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