Benzamide → Alpha-Hydroxyhippuric acid

HRID 20190

反応式

HRID 20190 の反応式
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:11]([OH:15])(=[O:14])[CH:12]=[O:13]>CC(C)=O>[C:1]([NH:9][CH:12]([OH:13])[C:11]([OH:15])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 2331BenzamideHCID 15620607Glyoxylic acid, monohydrate

生成物 1

HCID 450272Alpha-Hydroxyhippuric acid収率 100%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

The titled compound 65 was prepared according to a procedure described by Zoller et al.209 A 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.209 200-201° 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). νmax (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)+, C9H9NNaO4 requires 218.2.

後処理

  1. customThe titled compound 65 was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 19 h
  4. customThe reaction mixture was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-abf541aba12d43669516fde577f5d3de
出典データセット
uspto-grants-2010_06
特許番号
US07745573B2

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