Hydrochloric Acid → HCID 72579135、化合物

HRID 2375555ノート

反応式

HRID 2375555 の反応式
Cl.[NH2:2][OH:3].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[C:12]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH2:24])[CH2:17][CH2:16]1)(=[O:14])[CH3:13].Cl[C:26](Cl)(Cl)[CH:27]([OH:29])O>O>[C:12]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[NH:24][C:27](=[O:29])[CH:26]=[N:2][OH:3])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 27352321-(7-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one

生成物 1

HCID 72579135HCID 72579135、化合物収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

Intermediate 6 was synthesized according to the procedure described by Yang et al. (J. Am. Chem. Soc., 1996, 118, 9557). Hydroxylamine hydrochloride (7.10 g, 0.102 mol) and sodium sulfate (40 g, 0.28 mol) were taken up in 200 mL water and 10 mL 2 M aqueous hydrochloric acid in a 1 L round-bottomed flask, and 1-acetyl-7-amino-2,3-dihydro-(1H)-indole (5.0 g, 28 mmol) was added. Chloral hydrate (5.63 g, 34.0 mmol) was then added, and the flask covered with a rubber septum and nitrogen balloon and heated at 55° C. overnight. After cooling to room temperature, the isonitrosoacetanilide 6 was collected by filtration and dried under vacuum to give product of sufficient purity that it could be used in the next step (5.74 g, 82% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.30 (s, 3H) 3.07 (t, J=8.0 Hz, 2H) 4.13 (t, J=7.8 Hz, 2H) 7.09 (dd, J=7.3, 1.3 Hz, 1H) 7.14 (t, 1H) 7.48 (s, 1H) 7.73 (d, J=7.8 Hz, 1H) 10.76 (s, 1H) 12.33 (s, 1H).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe isonitrosoacetanilide 6 was collected by filtration
  3. customdried under vacuum
  4. customto give product of sufficient purity that it

出典と根拠

ORDレコード
ord-0bbb3b623f7a4281836086a0041966a3
出典データセット
uspto-grants-2008_12
特許番号
US07465798B2

反応ノート

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