ChemicalBook CAS DataBase List METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE

METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE synthesis

10synthesis methods

Product Name:METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE
CAS Number:4093-28-1
Molecular formula:C10H11NO4
Molecular Weight:209.2

75-36-5 Synthesis

75-36-5
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$17.92/100G

4136-97-4 Synthesis

4136-97-4
182 suppliers
$6.00/5g

4093-28-1
144 suppliers
$6.00/5g

Yield: 99%

Reaction Conditions:

with sodium hydrogencarbonate in water;ethyl acetate at 0 - 20; for 2.25 h;

Steps:

1.ii Step (ii)
Preparation of Methyl 4-acetylamino-2-hydroxy benzoate
A solution of Methyl 4-amino-2-hydroxy benzoate (50.7 grams, 303.6 mmol, obtained in above step) in ethyl acetate (750 mL) was added to a stirred solution of water (250 mL) and sodium bicarbonate (34.9 grams, 415.5 mmol) cooled at 0 °C followed by acetyl chloride (29.7 mL, 415.5 mmol) over a period of 15 minutes. The reaction mixture was gradually warmed to room temperature and stirred for 2 hours. The two layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to obtain methyl 4-acetylamino-2-hydroxy benzoate (63.5 grams).Yield: 99 %.Ή - NMR (CDC1₃): δ 10.86 (bs, 1H), 7.78 (d, J = 8.6 Hz, 1H), 7.23 (s, 1H), 7.16 (bs, 1H), 7.10 (d, J = 8.6 Hz, 1H), 6.13 (bs, 1H), 3.92 (s, 3H), 2.19 (s, 3H);Mass (m/z): 208 (M-H)⁺.

References:

SUVEN LIFE SCIENCES LIMITED;NIROGI, Ramakrishna;MOHAMMED, Abdul Rasheed;YARLGADDA, Suresh;RAVELLA, Srinivasa Rao;SHINDE, Anil Karbhari;KAMBHAMPATI, Ramasastri;ROAYALLEY, Praveen Kumar;JAYARAJAN, Pradeep;BHYRAPUNENI, Gopinadh;PATNALA, Sriramachandra Murthy;RAVULA, Jyothsna;JASTI, Venkateswarlu WO2013/42135, 2013, A1 Location in patent:Page/Page column 11