Hydroxyamine hydrochloride → 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime

HRID 1506276ノート

反応式

HRID 1506276 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2)=[CH2:2].Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>CO>[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[N:15][OH:16])[CH2:8][CH2:7][CH2:6]2)=[CH2:2]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 67167908HCID 67167908、化合物

生成物 1

HCID 866698666-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime収率 69%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To 6-vinyl-3,4-dihydronaphthalen-1(2H)-one (Intermediate I-1B, 1.6 g, 9.29 mmol) in methanol (10 mL) was sequentially added hydroxylamine hydrochloride (0.775 g, 11.15 mmol) and sodium acetate (0.915 g, 11.15 mmol). The reaction mixture was heated at 80° C. (oil bath temp.) for 1.5 h. The reaction mixture was concentrated under reduced pressure and to the residue was added water (30 mL). The contents were triturated and filtered. The solid material was washed with water (2×20 mL) and dried overnight to yield 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (1.2 g, 6.41 mmol, 69.0% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.81-1.94 (m, 2H) 2.71-2.87 (m, 4H) 5.23-5.32 (m, 1H) 5.78 (dd, J=17.61, 0.88 Hz, 1H) 6.69 (dd, J=17.61, 10.78 Hz, 1H) 7.18 (s, 1H) 7.28 (s, 1H) 7.85 (d, J=8.14 Hz, 1H) 8.23 (br. s., 1H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  2. additionwas added water (30 mL)
  3. customThe contents were triturated
  4. filtrationfiltered
  5. washThe solid material was washed with water (2×20 mL)
  6. customdried overnight

出典と根拠

ORDレコード
ord-17bec9994da8474b9e94aecc696aebd1
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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