Alternatived Products of [ 20628-18-6 ]
Product Details of [ 20628-18-6 ]
CAS No. : | 20628-18-6 |
MDL No. : | MFCD08448310 |
Formula : |
C9H10N2O4
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
210.19
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 20628-18-6 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 20628-18-6 ]
* 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.
- Upstream synthesis route of [ 20628-18-6 ]
- Downstream synthetic route of [ 20628-18-6 ]
- 1
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[ 20628-18-6 ]
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[ 16133-49-6 ]
Yield | Reaction Conditions | Operation in experiment |
100% |
Stage #1: 1-acetamido-5-methoxy-2nitrobenzene With hydrogenchloride In water Heating / reflux;
Stage #2: With sodium hydroxide; sodium hydrogencarbonate In water |
5-Methoxy-2-nitrophenylamine (Intermediate A59)
N-(3-methoxy-2-nitrophenyl)acetamide (Intermediate A58, 3.62 g, 0.0173 mol) was added to 6 N HCl (20 mL) heated to reflux and then cooled. The reaction mixture was filtered and the filtrate was basified with 1 N NaOH and saturated sodium bicarbonate then extracted with ethyl acetate. The solid was partitioned between ethyl acetate and saturated sodium bicarbonate. The two ethyl acetate layers were combined and washed twice with water. The ethyl acetate layer was concentrated under reduced pressure and dried to give 2.92 g (100%) of the title compound. |
85% |
With hydrogenchloride for 5h; Heating; |
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With sulfuric acid |
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With hydrogenchloride |
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With hydrogenchloride Heating; |
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Reference:
[1]Current Patent Assignee: ALEVIUM PHARMACEUTICALS - US2005/38076, 2005, A1
Location in patent: Page/Page column 26
[2]Zhang; Zhang, Zhoupeng; Tillekeratne; Hudson; Hudson, Richard A.
[Synthesis, 1996, # 3, p. 377 - 382]
[3]Reverdin; Widmer
[Chemische Berichte, 1913, vol. 46, p. 4074]
[4]Reverdin; Widmer
[Chemische Berichte, 1913, vol. 46, p. 4074]
[5]Acheson,R.M. et al.
[Journal of the Chemical Society. Perkin transactions I, 1978, p. 1117 - 1125]
- 2
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[ 16133-49-6 ]
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[ 20628-18-6 ]
Yield | Reaction Conditions | Operation in experiment |
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With acetic anhydride at 120℃; for 16h; |
C.1
A solution of 5-methoxy-2-nitroaniline (C-I) (25 g, 150 mmol, 1.0 eq) in acetic anhydride (45 ml, 480 mmol, 3.1 eq) was heated at 120 °C for 16 hours. The reaction mixture was cooled to room temperature, poured into water (500 ml) and the resulting precipitate was collected by filtration and dissolved in chloroform (250 ml). The organic layer was washed with water (250 ml) and brine (100 ml), then dried over sodium sulfate and concentrated to yield N-(5-methoxy- 2-nitrophenyl)acetamide (C-2) as a yellow solid. 1H NMR (400 MHz, DMSO): δ 10.30 (s, 1 H); 8.04 (d, J = 9.3 Hz, 1 H); 7.53 (d, J = 2.8 Hz, I H); 6.87 (dd, J - 9.3, 2.8 Hz, 1 H); 3.86 (s, 3 H); 2.13 (s, 3 H). LRMS m/z (M+H) 210.9 found, 21 1.1 required. |
- 3
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[ 20628-18-6 ]
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[ 69397-93-9 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: <i>N</i>-methyl-acetamide; ethyl acetate
2: hydrogenchloride; ethanol; water |
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- 4
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[ 20628-18-6 ]
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[ 1196074-43-7 ]