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

HRID 341116ノート

反応式

HRID 341116 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

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+)

後処理

  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

出典と根拠

ORDレコード
ord-91bd8ca4c2e34f56927177ba6fcf30ac
出典データセット
uspto-grants-2014_11
特許番号
US08895730B2

反応ノート

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