ChemicalBook CAS DataBase List ISOPROPYL 4-AMINOBENZOATE

ISOPROPYL 4-AMINOBENZOATE synthesis

9synthesis methods

Product Name:ISOPROPYL 4-AMINOBENZOATE
CAS Number:18144-43-9
Molecular formula:C10H13NO2
Molecular Weight:179.22

150-13-0 Synthesis

150-13-0
903 suppliers
$5.00/25g

67-63-0 Synthesis

67-63-0
1572 suppliers
$16.00/25ML

18144-43-9
85 suppliers
$34.00/1g

Yield: 100%

Reaction Conditions:

Stage #1:4-amino-benzoic acid;isopropyl alcohol with thionyl chloride at 20; for 90 h;Reflux;
Stage #2: with sodium hydrogencarbonate in water;isopropyl alcohol

Steps:

A.1.a
Method A; Example A-1; 4-({3-oxo-4-r2-(thfluoromethyl)benzyl1-3,4-dihvdro-2/-/-1 ,4-benzothiazin-2- vDmethvDbenzoic acid; Preparation of A-1 -a; 1 -methylethyl 4-aminobenzoate; To a solution of 4-aminobenzoic acid (5.0 g, 36.5 mmol) in 2-propanol (200 ml_) was added thionyl chloride (21 ml, 290 mmol). The mixture was first stirred at room temperature for 3 days and subsequently refluxed for 18 hrs. Carefully, an aqueous sodium bicarbonate solution (150 ml_) was added. It was extracted with ethyl acetate (3 x 80 ml_), dried over sodium sulfate, filtered, and concentrated to obtain a yellow solid in quantitative yield. ¹H-NMR (300 MHz, CDCI₃) δ ppm 7.8 (d, 2, Ar-H), 6.6 (d, 2H, Ar-H), 5.2 (q, 1 H, -CH(CHs)₂), 1.4 (d, 6H, CH(CH₃)₂).

References:

PFIZER INC.;CAMERON, Kimberly O'Keefe;KRAUSS, Achim Hans-Peter;LEFKER, Bruce Allen;NAIR, Sajiv Krishnan;PRASANNA, Ganesh;RUI, Eugene Yuanjin WO2010/116270, 2010, A1 Location in patent:Page/Page column 28-29