Home Cart 0 Sign in  

[ CAS No. 4031-84-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4031-84-9
Chemical Structure| 4031-84-9
Structure of 4031-84-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 4031-84-9 ]

Related Doc. of [ 4031-84-9 ]

Alternatived Products of [ 4031-84-9 ]

Product Details of [ 4031-84-9 ]

CAS No. :4031-84-9 MDL No. :MFCD00277666
Formula : C12H16N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 236.27 Pubchem ID :-
Synonyms :

Safety of [ 4031-84-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4031-84-9 ]

* 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.

  • Downstream synthetic route of [ 4031-84-9 ]

[ 4031-84-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 83909-55-1 ]
  • [ 4031-84-9 ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen In ethyl acetate for 12h;
97% With hydrogen In methanol 10.C Step C.10-4 10-5A solution of 10-4 (5.72 g, 21.5 mmol) in methanol was catalytically hydrogenated with Pd/C, then filtered and concentrated to dryness to afford the desired product 5-amino-2-morpholin-4-yl-benzoic acid methyl ester 10-5 (4.94 g, 97% yield); m/z = 237 (M+H)+.
97% With palladium 10% on activated carbon; hydrogen In ethanol for 48h; Methyl 5-amino-2-morpholinobenzoate 5 To a solution of methyl2-morpholino-5-nitrobenzoate 4 (9.30 g, 0.035 mol) in EtOH(50 mL) was added Pd on carbon (10 wt %, 0.93 g) and the reactionstirred under an atmosphere of hydrogen for 48 h. The reactionmixture was then filtered through a plug of Celite and the solventremoved in vacuo to give the title product 5 (8.04 g, 97%) as a paleyellow solid. m.p.: 119-121 °C (Lit [18]. 121-122 °C). RF: 0.39 (1:1petroleum ether-ethyl acetate). δH (400 MHz; CDCl3; Me4Si) 2.93(4H, t, J 4.0 Hz, N(CH2CH2)2O), 3.59 (2H, br s, NH2), 3.82 (4H, t,J 4.0 Hz, N(CH2CH2)2O), 3.87 (3H, s, OCH3), 6.77 (1H, dd, J 2.0,8.0 Hz, H-4), 6.95 (1H, d, J 8.0 Hz, H-3), 7.04 (1H, d, J 2.0 Hz, H-6). δC (100 MHz; CDCl3) 52.0 (OCH3), 53.6 (N(CH2CH2)2O), 67.3(N(CH2CH2)2O),117.5 (C-6),119.4 (C-4), 121.1 (C-3),127.4 (C-1),141.4(C-5), 144.2 (C-2), 168.1 (C]O). IR: νmax(ATR)/cm-1; 3452, 3365(NH), 2960 (CH aromatic), 2842 (CH alkane), 1700 (C=O ester),1628, 1498 (C=C aromatic), 1445, 1324 (CH alkane), 1243, 1112(C-O ether), 935, 825 (CH aromatic). m/z (ESI): 259 (MNa, 10%),237 (MH, 50), 205 (100). HRMS (ESI) Found (MNa):259.1051C12H16N2NaO3 requires 259.1053. Found (MH):237.1235C12H17N2O3 requires 237.1234. The 1H NMR data wasconsistent literature values [18].
97% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h;
97% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h;
74.9% With water; iron; ammonium chloride In tetrahydrofuran; ethanol at 100℃; for 2h; 1.3 A suspension of methyl 2-morpholino-5-nitrobenzoate (16.6 g, 62.4 mmol) obtained as a crude product in Step 2, reduced iron (17.4 g, 0.3 mol) and ammonium chloride (16.6 g, 0.3 mol) in tetrahydrofuran (160 ml), ethanol (320 ml) and water (80 ml) was heated under reflux at 100°C for 2 hr. After allowing to cool to room temperature, the mixture was filtered through celite and washed with ethanol. The solvent of the filtrate was evaporated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:3) to give methyl 5-amino-2-morpholinobenzoate (11.0 g, yield 74.9%).
With iron; ammonium chloride In tetrahydrofuran; methanol; water at 100℃; for 3h;
With hydrogen In ethyl acetate

Reference: [1]Location in patent: experimental part Chenna, Bala Chandra; King, Jason R.; Shinkre, Bidhan A.; Glover, Amanda L.; Lucius, Aaron L.; Velu, Sadanandan E. [European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 3752 - 3761]
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2009/80836, 2009, A2 Location in patent: Page/Page column 71
[3]Barker, David; Langley, Ries J.; Leung, Euphemia; Leung, Ivanhoe K. H.; Paulin, Emily K.; Pilkington, Lisa I.; Rees, Shaun W. P.; Reynisson, Jóhannes; Sparrow, Kevin; Xu, Chris Sun; van Rensburg, Michelle [European Journal of Medicinal Chemistry, 2020, vol. 191]
[4]Rees, Shaun W.P.; Leung, Euphemia; Reynisson, Jóhannes; Barker, David; Pilkington, Lisa I. [Bioorganic Chemistry, 2021, vol. 114]
[5]Rees, Shaun W. P.; Rees, Tayla A.; Leung, Euphemia; Walker, Christopher S.; Barker, David; Pilkington, Lisa I. [International Journal of Molecular Sciences, 2021, vol. 22, # 21]
[6]Current Patent Assignee: JAPAN TOBACCO INC - EP1688420, 2006, A1 Location in patent: Page/Page column 119-120
[7]Hirashima, Shintaro; Oka, Takahiro; Ikegashira, Kazutaka; Noji, Satoru; Yamanaka, Hiroshi; Hara, Yoshinori; Goto, Hiroyuki; Mizojiri, Ryo; Niwa, Yasushi; Noguchi, Toru; Ando, Izuru; Ikeda, Satoru; Hashimoto, Hiromasa [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3181 - 3186]
[8]Chenna, Bala Chandra; Shinkre, Bidhan A.; King, Jason R.; Lucius, Aaron L.; Narayana, Sthanam V.L.; Velu, Sadanandan E. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 380 - 385]
Same Skeleton Products
Historical Records