ChemicalBook CAS DataBase List ALPHA-HYDROXYHIPPURIC ACID

ALPHA-HYDROXYHIPPURIC ACID synthesis

5synthesis methods

Product Name:ALPHA-HYDROXYHIPPURIC ACID
CAS Number:16555-77-4
Molecular formula:C9H9NO4
Molecular Weight:195.17

55-21-0 Synthesis

55-21-0
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298-12-4 Synthesis

298-12-4
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16555-77-4
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$14.14/500mgs:

Yield:16555-77-4 100%

Reaction Conditions:

in water;acetone; for 19 h;Heating / reflux;

Steps:

7.7.3

The titled compound 65 was prepared according to a procedure described by Zoller et al.²⁰⁹A mixture of benzamide 35 (5.00 g, 41.3 mmol) and glyoxylic acid monohydrate 41 (4.32 g, 46.9 mmol) in anhydrous acetone (70 mL) was heated at reflux for 19 h. The reaction mixture was evaporated under reduced pressure to afford the desired product 65 as a colourless solid (8.06 g, 100%), m.p. 198-200° C. (lit.²⁰⁹200-201° C. (dec)) Spectroscopic data indicated the crude product 65 did not require purification and was used directly in the subsequent reaction (Section 7.11.4). ν_max(KBr): 3310bs, 3058w, 1728s, 1646s, 1602w, 1582w, 1535s, 1491w, 1452w, 1315m, 1292w, 1254m, 1161m, 1097s, 1040m, 1002w, 957m, 805w, 770w, 728m, 692m, 654m, 609w, 515m, 483w cm^-1. ¹H n.m.r. (300 MHz, D₆-DMSO): δ 5.60 (d, J=7.8 Hz, 1H, H2), 7.41-7.49 (m, 2H, H3', 5'), 7.55 (m, 1H, H4'), 7.86-7.92 (m, 2H, H2', 6'), 9.26 (d, J=7.8 Hz, 1H, NH), two exchangeable OH protons not observed. ¹³C n.m.r. (75 MHz, D₆-DMSO): δ 71.7 (C2), 127.6, 128.3, 131.7 (Arom CH), 133.7 (C1'), 166.0, 171.5 (C1, CONH). Mass Spectrum (ESI⁺, MeOH): m/z 218.2 (M+Na)⁺, C₉H₉NNaO₄requires 218.2.