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Structure of 353525-11-8

Chemical Structure| 353525-11-8

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Product Details of [ 353525-11-8 ]

CAS No. :353525-11-8
Formula : C9H11NO3
M.W : 181.19
SMILES Code : O=C(OC)CC1=CC=C(N)C(O)=C1
MDL No. :MFCD20694774
InChI Key :LZGUTYHAHOXRTO-UHFFFAOYSA-N
Pubchem ID :17858854

Safety of [ 353525-11-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 353525-11-8 ]

* 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 [ 353525-11-8 ]

[ 353525-11-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 353525-11-8 ]
  • [ 21908-53-2 ]
  • [ 175205-39-7 ]
  • methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In methanol; chloroform; ethyl acetate; (Step 1) Synthesis of methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate In methanol (50 ml), <strong>[175205-39-7]5-fluoro-2-methylphenyl isothiocyanate</strong> (2.00 g, 12.0 mmol) was added to methyl 4-amino-3-hydroxyphenylacetate (2.17 g, 12.0 mmol) at room temperature. After stirring for 27 hours, mercuric oxide (yellow) (3.12 g, 14.4 mmol) was added to the reaction mixture and the resulting mixture was heated at 70ØC for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was washed with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 46%) was obtained as a pale brown oil. 1H-NMR (CDCl3) δ: 2.13 (s, 3H), 3.705 (s, 2H), 3.711 (s, 3H), 6.74 (dt, J=8.3,2.7Hz, 1H), 6.81 (br, 1H), 7.15 (dd, J=8.1,1.7Hz, 2H), 7.31 (d, J=1.2Hz, 1H), 7.44 (d, J=8.1Hz, 1H), 8.09 (dd, J=11.0,2.7Hz, 1H). MS (ESI) m/z 315 (M++1).
46% In methanol; chloroform; ethyl acetate; (Step 1) Synthesis of methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate In methanol (50 ml), <strong>[175205-39-7]5-fluoro-2-methylphenyl isothiocyanate</strong> (2.00 g, 12.0 mmol) was added to methyl 4-amino-3-hydroxyphenylacetate (2.17 g, 12.0 mmol) and the resulting mixture was stirred at room temperature for 27 hours. Mercuric oxide (yellow) (3.12 g, 14.4 mmol) was added to the reaction mixture, followed by stirring at 70ØC for 4 hours. After cooling to room temperature, the reaction mixture was filtered through Celite, followed by washing with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate (1.73 g, 46%) was obtained as a brown oil. 1H-NMR (CDCl3) δ: 2.13 (s, 3H), 3.705 (s, 2H), 3.711 (s, 3H), 6.74 (dt, J=8.3,2.7Hz, 1H), 6.81 (br, 1H), 7.15 (dd, J=8.1, 1.7Hz; 2H), 7.31 (d, J=1.2Hz, 1H), 7.44 (d, J=8.1Hz, 1H), 8.09 (dd, J=11.0,2.7Hz, 1H). MS (ESI) m/z 315 (M++1).
  • 2
  • [ 353525-11-8 ]
  • [ 175205-39-7 ]
  • methyl (2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl)acetate [ No CAS ]
  • 3
  • [ 353525-11-8 ]
  • [ 171919-36-1 ]
  • [ 441716-30-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: A mixture of 6-fluoro-1-methylindole-3-carbaldehyde (13a) (500 mg, 2.82 mmol) and methyl 4-amino-3-hydroxyphenylacetate (11a) (767 mg, 4.23 mmol) in EtOH (15 ml) was stirred for 22 h, and iodobenzene diacetate (1.09 g, 3.38 mmol) was added portionwise to the mixture. After being stirred for 1 h, the mixture was concentrated, and the residue was purified column chromatography with n-hexane-AcOEt (1:1, v/v) as eluent to give methyl [2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl]acetate (889 mg, 93%) as a brown solid.
 

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