[ CAS No. 86499-96-9 ]

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Product Details

CAS No. :86499-96-9MDL No. :MFCD03085918
Formula :C10H10BrNOInChI Key :JMXPGCGROVEPID-UHFFFAOYSA-N
M.W :240.10Pubchem ID :2757184
Boiling Point :383.2°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 29.1 H-Bond Acceptor Count : 1
XLogP3 : 2.3 H-Bond Donor Count : 1
SP3 : 0.30 Rotatable Bond Count : 0

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 86499-96-9 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
70.1%
Stage #1: With phosphorus pentachloride; iodine In chloroform at 0℃; for 0.50 h;
Stage #2: With bromine In chloroform at 0 - 20℃; for 4.00 h; Refluxed
A solution of Part A(1) compound (1.0 g, 6.20 mmoles) in dry CHCl3 (15 ml) was cooled down to 0° C. (ice-salt bath), treated with PCl5 (1.5 g, 7.20 mmoles) followed by I2 (15 mg) then stirred at 0° C. under argon for 30 minutes. The yellow solution was treated with Br2 (0.39 ml or 1.2 g, 7.51 mmoles), warmed up to room temperature and refluxed under argon for 4.0 hours. The mixture was then poured into ice-water (20 g), stirred and the phases were separated, washing the aqueous phase with CHCl3 (25 ml). The combined organic extracts were washed with H2O (5.0 ml), dried (anhydrous MgSO4), filtered, evaporated to dryness and dried in vacuo. The crude product mixture was chromatographed on a silica gel column (Merck, 70 g), eluting the column with EtOAc:Hexane (1:9) to give title compound as off-white precipitates (1.137 g., m.pt. 170-172°, 70.1percent) with consistent 1H-NMR and 13C-NMR spectral data. [00180] TLC: Rf 0.13 (Silica gel; EtOAc:Hexane-1:4; UV).
Reference: [1] Patent: US6777550, 2004, B1. Location in patent: Page column 28
[2] Patent: US4575503, 1986, A
[3] Patent: US4410520, 1983, A
[4] Patent: US4473575, 1984, A
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3488 - 3494
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YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 60℃; for 20.00 h;
10 parts by weight of the heated melted polyphosphoric acid was added to the drying kettle, With stirring, The above 2-bromo-3,4-dihydro-N-hydroxy- (2H) -naphthalimide was added in portions at a temperature of 60 ° C, Insulation reaction for 20 hours; The reaction solution was added dropwise to 12.5 parts by weight of water to carry out hydrolysis, Still Washed to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one crude; 10 parts by weight of methanol and 0.1 part by weight of activated carbon were added, Heating decolorization, After filtration, the filtrate was cooled to 10 ° C for 20 hours, centrifuged, washed and dried to give 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one. The purity of the product was 3, 10-bromo-1,3,4,5-tetrahydro-2H-1-benzazepan-2-one as high as 99.6percent and the yield was as high as 98percent.
Reference: [1] Patent: CN105017154, 2017, B. Location in patent: Paragraph 0032; 0050-0051; 0056-0057
[2] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1545 - 1552
[3] Patent: US5677297, 1997, A
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3488 - 3494
[2] Patent: CN105017154, 2017, B
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Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1545 - 1552
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Reference: [1] Patent: CN105017154, 2017, B
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