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Chemical Structure| 446-32-2 Chemical Structure| 446-32-2
Chemical Structure| 446-32-2

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Product Details of 2-Amino-4-fluorobenzoic acid

CAS No. :446-32-2
Formula : C7H6FNO2
M.W : 155.13
SMILES Code : O=C(O)C1=CC=C(F)C=C1N
MDL No. :MFCD00075553
InChI Key :LGPVTNAJFDUWLF-UHFFFAOYSA-N
Pubchem ID :2724967

Safety of 2-Amino-4-fluorobenzoic acid

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

Application In Synthesis of 2-Amino-4-fluorobenzoic acid

* 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 [ 446-32-2 ]
  • Downstream synthetic route of [ 446-32-2 ]

[ 446-32-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 446-32-2 ]
  • [ 117324-05-7 ]
YieldReaction ConditionsOperation in experiment
94% With thionyl chloride In ethanol A.
Synthesis of ethyl 2-amino-4-fluorobenzoate
To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol).
The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
94% With thionyl chloride In ethanol A.
Synthesis of ethyl 2-amino-4-fluorobenzoate
To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol).
The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
References: [1] Patent: US2002/77486, 2002, A1, .
[2] Patent: US6906063, 2005, B2, .
[3] Patent: EP1380576, 2004, A1, . Location in patent: Page 97.
  • 2
  • [ 64-17-5 ]
  • [ 446-32-2 ]
  • [ 117324-05-7 ]
YieldReaction ConditionsOperation in experiment
94% for 96 h; Reflux A. Synthesis of ethyl 2-amino-4-fluorobenzoate (0244) To a chilled solution of 2-amino-4-fluorobenzoic acid (1.57 g, 10.1 mmol) in absolute ethanol (20 mL) was added neat thionyl chloride (4.4 mL, 60 mmol). The reaction mixture was refluxed for 4 days total, with addition of more SOCl2 (8 mL, 110 mmol), then concentrated, diluted with EtOAc, washed with 2N NaOH, dried and concentrated in vacuo to give ethyl 2-amino-4-fluorobenzoate (1.73 g, 94percent).
References: [1] Patent: EP2314593, 2016, B1, . Location in patent: Paragraph 0243; 0244.
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3772 - 3793.
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 10, p. 5803 - 5814.
 

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