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

HRID 1028330노트

반응식

HRID 1028330 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 alternate, 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 hours, cooled, and filtered. The filtrate was worked up by extraction into toluene, washing the extract with water and bicarbonate solution, drying, and concentrating. The residue was combined with the formic acid-insoluble solids and chromatographed over silica gel. Obtained were the desired nitrile product, 1.58 g (49%), m.p. 85-87° C., mass spec (m/z): 325, 327 (M+); the amide byproduct, 0.42 g (12%), m.p. 179-184° C., mass spec (m/z): 343, 345 (M+); and the oxime byproduct, m.p. 104-107° C., 0.17 g (5%), mass spec (m/z): 343 (M+).

후처리

  1. customAn alternate, but less satisfactory synthesis
  2. temperatureat reflux for 2 hours
  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. concentrationconcentrating
  10. customchromatographed over silica gel
  11. customObtained

출처 및 근거

ORD 기록
ord-0f6c7b919b304f79b803bba883067a1a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735528B1

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