4-Hydroxybenzoic acid hydrazide → 4-Hydroxy-benzoic acid (4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-hydrazide

HRID 1667564

반응식

HRID 1667564 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[Br:12][C:13]1[C:14]([CH3:21])=[C:15]([CH:19]=O)[NH:16][C:17]=1[CH3:18]>C(O)(=O)C.CCO>[Br:12][C:13]1[C:14]([CH3:21])=[C:15]([CH:19]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)[NH:16][C:17]=1[CH3:18]

참가 물질

5

반응물 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 447184324-Bromo-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

생성물 1

HCID 1363301314-Hydroxy-benzoic acid (4-bromo-3,5-dimethyl-1H-pyrrol-2-ylmethylene)-hydrazide수율 77%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 702Ethanol용매

실험 절차

To a solution of 4-hydroxy-benzoic acid hydrazide (0.06 g, 0.0004 mol) and 4-bromo-3,5-dimethyl-pyrrole-2-carboxaldehyde (0.08 g, 0.0004 mol) in abs. EtOH (5 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 5 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give red solid 0.1 g, in 77% yield, mp: 235.4° C. 1H NMR (DMSO-d6) δ 11.46 (s, 1H), 11.21 (s, 1H), 9.99 (s, 1H), 8.26 (s, 1H), 7.76 (d, 2H), 6.82 (d, 2H), 2.15 (s, 3H), 2.03 (s, 3H). 13C NMR (DMSO-d6) δ 163.9, 162.2, 140.2, 131.6, 131.3, 126.1, 124.0, 124.3, 116.8, 13.4, 11.8. Anal. Calcd for C14H14BrN3O2.¼H2O: C, 49.35; H, 4.14; N, 12.33; Br, 23.69. Found: C, 49.21; H, 3.95; N, 11.96; Br, 23.37.

후처리

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationconcentrated
  3. customto remove solvent

출처 및 근거

ORD 기록
ord-47a4654638cc4db98bc416e4ee7446fc
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044241B2

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