ChemicalBook CAS DataBase List 3-AMINO-1,1'-BIPHENYL-4-CARBOXYLICACID

3-AMINO-1,1'-BIPHENYL-4-CARBOXYLICACID synthesis

11synthesis methods

Product Name:3-AMINO-1,1'-BIPHENYL-4-CARBOXYLICACID
CAS Number:4445-43-6
Molecular formula:C13H11NO2
Molecular Weight:213.23

20776-50-5

98-80-6

4445-43-6

Pd(PPh3)4 (0.052 g, 0.045 mmol) was added to degassed DMF (10 mL) and 1 M K2CO3 aqueous solution (7 mL) under nitrogen protection using 2-amino-4-bromobenzoic acid (0.992 g, 4.46 mmol) and phenylboronic acid (0.832 g, 6.69 mmol). The reaction mixture was stirred at 80 °C for 16 hours. Upon completion of the reaction, DMF was removed under reduced pressure.The residue was dissolved in 4 N NaOH aqueous solution (40 mL) and the aqueous phase was washed twice with ethyl acetate (2 x 50 mL). The pH of the aqueous phase was adjusted to 5 by the addition of 4 N HCl. Subsequently, the aqueous phase was extracted three times with ethyl acetate (3 x 50 mL) and once with DCM-MeOH (9:1, 50 mL). All organic phases were combined, dried with MgSO4, and the solvent was evaporated under reduced pressure to give a beige solid. The solid was ground in ether, filtered and dried to give 3-amino-[1,1'-biphenyl]-4-carboxylic acid as a beige solid (0.721 g, 76% yield). mS (ESI, m/z): 214.3 [M + H+] C13H11NO2; tR = 0.78 min.

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4445-43-6
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Yield:4445-43-6 95.9%

Reaction Conditions:

with water;sodium hydroxide in tetrahydrofuran at 25; for 12 h;Reagent/catalyst;Solvent;

Steps:

285; 308 Synthesis of compound 285.1.

Into a 100-mL round-bottom flask, was placed 249.1 (200 mg, 0.880 mmol, 1 equiv), H₂O (5 mL), THF (5 mL), and NaOH (351.9 mg, 8.800 mmol, 10 equiv). The resulting solution was stirred for 12 h at 25 ^oC. The reaction was then quenched by the addition of 20 mL of dilute hydrochloric acid. The resulting solution was extracted with 3 x 30 mL of ethyl acetate, and the combined organic layers were concentrated under vacuum. This resulted in 180 mg (95.9%) of 285.1 as a yellow solid.

References:

WO2020/97408,2020,A1 Location in patent:Paragraph 00842; 00897

20776-50-5 Synthesis

20776-50-5
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98-80-6 Synthesis

98-80-6
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4445-43-6
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$32.00/100mg

References

109497-00-9 Synthesis