Hydroxyamine hydrochloride → 7-Bromo-9,9-diethylfluorene-2-carbonitrile

HRID 341116노트

반응식

HRID 341116 반응식
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH:19]=O)=[CH:10][C:11]=3[C:12]2([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1.Cl.[NH2:22]O>C(O)=O>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([C:19]#[N:22])=[CH:10][C:11]=3[C:12]2([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 154763497-Bromo-9,9-diethylfluorene-2-carboxaldehyde

생성물 1

HCID 710290647-Bromo-9,9-diethylfluorene-2-carbonitrile

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

An alternative but less satisfactory synthesis was conducted as follows: A mixture of 7-bromo-9,9-diethylfluorene-2-carboxaldehyde (3.29 g, 10.0 mmol), hydroxylamine hydrochloride (0.9 g, 10.0 mmol), and formic acid (15 mL), was held at reflux for 2 hr, cooled and filtered. The filtrate was worked up by extraction into toluene, washing the extract with water, and bicarbonate solution, drying and concentration. The residue was combined with the formic acid-insoluble solids and chromatographed over silica gel. There were obtained, the desired aldehyde product, 1.58 g (49%), m.p. 85-87° C., mass spectrum (m/z): 325, 327 (M+); the amide by-product, 0.42 g (12%), m.p. 179-184° C., mass spectrum (m/z): 343,345 (M+); and the oxime by-product, m.p. 104-107° C., 0.17 g (5%), mass spectrum (m/z): 343 (M+)

후처리

  1. customAn alternative but less satisfactory synthesis
  2. temperatureat reflux for 2 hr
  3. temperaturecooled
  4. filtrationfiltered
  5. extractionThe filtrate was worked up by extraction into toluene
  6. washwashing the
  7. extractionextract with water, and bicarbonate solution
  8. customdrying
  9. concentrationconcentration
  10. customchromatographed over silica gel
  11. customThere were obtained

출처 및 근거

ORD 기록
ord-91bd8ca4c2e34f56927177ba6fcf30ac
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895730B2

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