Sodium Hydroxide → Phenyl(pyridazin-4-yl)methanone

HRID 339710

반응식

HRID 339710 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:14].[Na+]>C(O)(=O)C>[C:2]1([C:1]([C:8]2[CH:13]=[CH:12][N:11]=[N:10][CH:9]=2)=[O:14])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 5984154-Benzylpyridazine

생성물 1

HCID 12486783Phenyl(pyridazin-4-yl)methanone

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
100 °C

실험 절차

To a 100° C. suspension of SeO2 (4.75 g, 0.043 mole) in acetic acid (216 mL) was added dropwise to a solution of 4-benzylpyridazine (11; 7.6 g, 0.044.6 mole) in acetic acid (216 mL). The mixture was heated for 1 hour at 100° C. The reaction mixture was cooled to room temperature and was neutralized to a pH ˜6-7 with 50% NaOH. The neutralized mixture was extracted twice with CH2Cl2. The combined extracts were dried over MgSO4 and were evaporated to dryness. The crude product was purified by crystallization in refluxing isopropyl alcohol (10 vol). The yield of phenylpyridazin-4-yl-methanone (12) obtained was 5.8 g or 66%. MS (ESI+): [M+H]+=185.33; 1H NMR (300 MHz, CDCl3), δ ppm: 7.5-7.60 (m, 2H), 7.64-7.83 (m, 4H), 9.42-9.51 (m, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe neutralized mixture was extracted twice with CH2Cl2
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customwere evaporated to dryness
  5. customThe crude product was purified by crystallization
  6. temperaturein refluxing isopropyl alcohol (10 vol)

출처 및 근거

ORD 기록
ord-7d2ea79406194ab58aad7f311b3f3114
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895556B2

연결된 노트

불러오는 중…