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[ CAS No. 61090-37-7 ]

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Chemical Structure| 61090-37-7
Chemical Structure| 61090-37-7
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CAS No. :61090-37-7 MDL No. :MFCD06659470
Formula : C8H9NO Boiling Point : 268.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :135.16 g/mol Pubchem ID :11701043
Synonyms :

Safety of [ 61090-37-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 61090-37-7 ]

  • Upstream synthesis route of [ 61090-37-7 ]
  • Downstream synthetic route of [ 61090-37-7 ]

[ 61090-37-7 ] Synthesis Path-Upstream   1~6

  • 1
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  • [ 61090-37-7 ]
YieldReaction ConditionsOperation in experiment
67.7% With hydrogen bromide In water at 110℃; for 16 h; Synthesis of 4-amino-2,3-dihydrobenzofuran (1c)
The compound 1b (4.10 g, 16.3 mmol) was dissolved in hydrobromic acid (HBr) (48percent aqueous, 20.0 mL, commercial product), and the mixed solution was stirred by heating at 110°C for 16 hours.
After the mixed solution was allowed to cool to room temperature, sodium hydroxide granules were gradually added at 0°C so that the pH was adjusted to about 9.
Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (50 mL * 4).
The combined organic layer was dried over sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure.
The residue was purified by a medium-pressure column chromatography (Smart Flash EPCLC W-Prep 2XY system) (n-hexane/EtOAc =1/1), and thus 4-amino-2,3-dihydrobenzofuran (compound 1c) (1.49 g, 11.0 mmol, 67.7percent) was obtained as a colorless solid.
TLC Rf = 0.30 (n-hexane/EtOAc = 1/1)
1H NMR (400 MHz, CDCl3) δ 6.94 (dd, J = 8.4, 8.4 Hz, 1H), 6.28 (dd, J = 0.4, 7.6 Hz, 1H), 6.23 (dd, J = 0.4, 7.6 Hz, 1H), 4.59 (t, J = 8.4 Hz, 2H), 3.60 (brs, 2H), 3.02 (t, J = 8.4 Hz, 2H)
67.6% With water; hydrogen bromide In neat (no solvent) at 20 - 110℃; for 16 h; Synthesis of 4-amino-2,3-dihydrobenzofuran (1c)
The compound 1b (4.10 g, 16.3 mmol) was dissolved in hydrobromic acid (HBr) (48percent aqueous, 20.0 mL, commercial product), and the mixed solution was stirred by heating at 110° C. for 16 hours.
After the mixed solution was allowed to cool to room temperature, sodium hydroxide granules were gradually added at 0° C. so that the pH was adjusted to about 9.
Subsequently, the mixture was extracted with ethyl acetate (EtOAc) (50 mL*4).
The combined organic layer was dried over sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure.
The residue was purified by a medium-pressure column chromatography (Smart Flash EPCLC W-Prep 2XY system) (n-hexane/EtOAc=1/1), and thus 4-amino-2,3-dihydrobenzofuran (compound 1c) (1.49 g, 11.0 mmol, 67.6percent) was obtained as a colorless solid.
TLC Rf=0.30 (n-hexane/EtOAc=1/1)
1H NMR (400 MHz, CDCCl3) δ (6.94 (dd, J=8.4, 8.4 Hz, 1H), 6.28 (dd, J=0.4, 7.6 Hz, 1H), 6.23 (dd, J=0.4, 7.6 Hz, 1H), 4.59 (t, J=8.4 Hz, 2H), 3.60 (brs, 2H), 3.02 (t, J=8.4 Hz, 2H)
40%
Stage #1: With hydrogen bromide In water at 100℃;
Stage #2: With sodium hydroxide In water
Synthesis of 2,3-dihydrobenzofuran-4-amine
Into a 210 mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide (10.5 g, 41.83 mmol, 1.00 equiv).
To the mixture was added HBr (48percent) (100 mL).
The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 100° C. in a bath of oil.
The reaction progress was monitored by TLC (EtOAc/PE=1:2).
Adjustment of the pH to 9 was accomplished by the addition of NaOH.
The resulting solution was extracted with EtOAc and the organic layers combined.
The resulting mixture was washed with H2O.
The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator.
This resulted in 2.5 g (40percent) of 2,3-dihydrobenzofuran-4-amine as yellow oil.
40%
Stage #1: With hydrogen bromide In water at 100℃; for 16 h;
Stage #2: With sodium hydroxide In water
Concentrated hydrobromic acid (100 mL) was added to N-(2-(2-hydroxyethyl)-3- methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100 °C for 16 h. The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4-amine in 40percent yield as yellow oil.
40%
Stage #1: With hydrogen bromide In water at 100℃;
Stage #2: With sodium hydroxide In water
Synthesis of 2,3-dihydrobenzofuran-4-amine
Into a 210 mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide (10.5 g, 41.83 mmol, 1.00 equiv).
To the mixture was added HBr (48percent) (100 mL).
The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 100° C. in a bath of oil.
The reaction progress was monitored by TLC (EtOAc/PE=1:2).
Adjustment of the pH to 9 was accomplished by the addition of NaOH.
The resulting solution was extracted with EtOAc and the organic layers combined.
The resulting mixture was washed with H2O.
The mixture was dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator This resulted in 2.5 g (40percent) of 2,3-dihydrobenzofuran-4-amine as yellow oil.
40%
Stage #1: at 100℃; for 16 h;
Stage #2: With sodium hydroxide In water
4. Synthesis of 2,3-dihydrobenzofuran-4-amine; Concentrated hydrobromic acid (100 mL) was added to N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100° C. for 16 h. The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3.x.100 mL). The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4-amine in 40percent yield as yellow oil.
40%
Stage #1: With hydrogen bromide In water at 100℃; for 16 h;
Stage #2: With sodium hydroxide In water
4. Synthesis of 2,3-dihydrobenzofuran-4-amine.Concentrated hydrobromic acid (100 mL) was added to iV-(2-(2-hydroxyethyl)-3- methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100 0C for 16 h. The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4- amine in 40percent yield as yellow oil.
40%
Stage #1: at 100℃; for 16 h;
Concentrated hydrobromic acid (100 mL) was added to N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100° C. for 16 h. The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3.x.100 mL). The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4-amine in 40percent yield as yellow oil.
40%
Stage #1: at 100℃; for 16 h;
4. Synthesis of 2,3-dihvdrobenzofuran-4-amine.Concentrated hydrobromic acid (100 mL) was added to 7v~-(2-(2-hydroxyethyl)-3- methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100 °C for 16 h. The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4- amine in 40percent yield as yellow oil.
40%
Stage #1: With hydrogen bromide In water at 100℃; for 16 h;
Stage #2: With sodium hydroxide In water
Concentrated hydrobromic acid (100 mL) was added to N-(2-(2-hydroxyethyl)-3-methoxyphenyl)pivalamide (41.8 mmol) and the reaction mixture was heated at 100° C. for 16 h.
The pH of the solution was adjusted to 9 with solid sodium hydroxide and the solution was extracted with ethyl acetate (3*100 mL).
The combined organic layers were was washed with water (50 mL), dried (sodium sulfate), and concentrated to provide 2,3-dihydrobenzofuran-4-amine in 40percent yield as yellow oil.

Reference: [1] Patent: EP2881397, 2015, A1, . Location in patent: Paragraph 0053; 0058; 0059
[2] Patent: US2016/303089, 2016, A1, . Location in patent: Paragraph 0161; 0168; 0169; 0170; 0171
[3] Patent: US2008/318941, 2008, A1, . Location in patent: Page/Page column 39
[4] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 127-128
[5] Patent: US2008/200471, 2008, A1, . Location in patent: Page/Page column 60; 61-62
[6] Patent: US2010/16297, 2010, A1, . Location in patent: Page/Page column 35
[7] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 93
[8] Patent: US2010/29629, 2010, A1, . Location in patent: Page/Page column 61
[9] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 111
[10] Patent: US2010/22581, 2010, A1, . Location in patent: Page/Page column 45; 46
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: With hydrogen bromide In water; acetic acid at 20℃; for 4 h; Heating / reflux
Stage #2: With sodium hydroxide In water; acetic acid
2-(2'-Hydroxyethyl)-3-methoxy-N-tert-butoxycarbonyl-aniline (158 g, 0.59 mol) was added portionwise to a stirred solution of hydrogen bromide in acetic acid (30percent, 1.7 L) at room temperature.
The reaction was then heated to reflux for 4 h.
The reaction mixture was cooled to room temperature, basified to pH 14 with aqueous sodium hydroxide solution (6 N) and extracted with dichloromethane (3*2 L).
The organic extracts were combined, dried (magnesium sulphate) and evaporated to give the title compound as an orange oil (78 g, 92percent); NMR (400 MHz, CDCl3) δH 2.99 (2H, t, J 8.5 Hz), 3.55 (2H, br s), 4.57 (2H, t, J 8.5 Hz), 6.19 (1H, d, J 7.5 Hz), 6.25 (2H, d, J 7.5 Hz), 6.92 (1H, t, J 8.0 Hz); IR νmax (Nujol)/cm-1 2853, 2610, 1544, 1462, 1262, 1234, 986 and 761.
Reference: [1] Patent: US2005/187282, 2005, A1, . Location in patent: Page/Page column 9-10
[2] Tetrahedron Letters, 2007, vol. 48, # 17, p. 3039 - 3041
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Reference: [1] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 52
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Reference: [1] Patent: US3963717, 1976, A,
  • 5
  • [ 536-90-3 ]
  • [ 61090-37-7 ]
Reference: [1] Patent: EP2881397, 2015, A1,
[2] Patent: US2016/303089, 2016, A1,
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  • [ 56619-93-3 ]
  • [ 61090-37-7 ]
Reference: [1] Patent: EP2881397, 2015, A1,
[2] Patent: US2016/303089, 2016, A1,
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