Hydrochloric Acid → N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamide

HRID 2229532

反応式

HRID 2229532 の反応式
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:10]=3[O:9]C2=O)=[C:4]([F:23])[CH:3]=1.[OH-].[K+].Cl>C(O)C>[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:12](=[O:13])[C:11]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:10]=2[OH:9])=[C:4]([F:23])[CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 184681743-(4-Bromo-2-fluoro-benzyl)-7-methoxy benzo[e][1,3]oxazine-2,4-dione

生成物 1

HCID 18468133N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamide収率 71%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

solution of 3-(4-bromo-2-fluoro-benzyl)-7-methoxy benzo[e][1,3]oxazine-2,4-dione (1.67 g, 4.4 mmol) in ethanol (80 ml, 0.06 M) was cooled to 0° C. and treated with aq KOH (0.673 g, 11.9 mmol, 1.2 M). After 3 h, the reaction was acidified to pH 1-2 with 2 N HCl and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated. The crude solid was recrystallized from heptane and ethyl acetate to give N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methoxy-benzamide as a white crystalline solid (1.10 g, 71%): mp 128-129.5° C.; Rf 0.28 (25% ethyl acetate in heptane); 1H NMR (DMSO-d6 300 MHz) δ 12.70 (br s, 1H), 9.14 (br t, J=5.2 Hz, 1H), 7.80 (d; J=8.5 Hz, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.40-7.25 (m, 2H), 6.50-6.48 (m, 2H), 4.45 (d, J=5.2 Hz, 2H), 3.75 (s, 3H). ESI-LC/MS m/z calcd for C15H13BrFNO2: 353.0; found 352.0 (M−1)−. Anal. calcd for C15H13BrFNO2: C, 50.87; H, 3.70; N, 3.95. Found C, 50.70; H, 3.73; N, 3.91.

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid was recrystallized from heptane and ethyl acetate

出典と根拠

ORDレコード
ord-e9d8ab47e94141b2951c640e1c8b242b
出典データセット
uspto-grants-2002_07
特許番号
US06420426B1

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