Hydrochloric Acid → 2-Hydroxyimino-N-indan-5-yl-acetamide

HRID 2353924

反応式

HRID 2353924 の反応式
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[NH2:20][OH:21].[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2.Cl>O>[OH:21][N:20]=[CH:2][C:3]([NH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2)=[O:5]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 90496Indan-5-amineHCID 159255Hydroxylamine, sulfate (1:1)

生成物 1

HCID 722820052-Hydroxyimino-N-indan-5-yl-acetamide収率 81.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
45 °C

実験手順

To a solution of chloral hydrate (5.56 g, 33.63 mmol) and anhydrous sodium sulfate (28.58 g, 201.20 mmol) in water (90 mL) add a mixture of hydroxylamine sulfate (25.63 g, 156.16 mmol), 5-aminoindane (4 g, 30.03 mmol), concentrated hydrochloric acid (3.14 mL) in water (30 mL). Heat the mixture at 45° C. for 1 h and at 75° C. for 2 hr. Cool the mixture to room temperature and filter the solid. Wash the solid with water and ethyl ether. Dry the solid under vacuum to yield the title compound (4.98 g, 81%). 1H NMR (DMSO-d6, 300 MHz) δ 1.90 (quintuplet, J=7.8 Hz, 2H), 2.72 (q, J=7.8 Hz, 4H), 7.06 (d, J=8.2 Hz, 1H), 7.28 (dd, J=1.5, 8.2 Hz, 1H), 7.49 (bs, 1H), 9.94 (s, 1H), 12.02 (s, 1H). MS (ES−): 203 (M−H).

後処理

  1. temperatureCool the mixture to room temperature
  2. filtrationfilter the solid
  3. washWash the solid with water and ethyl ether
  4. customDry the solid under vacuum

出典と根拠

ORDレコード
ord-fc9a7b84854d4c3a840555f158a5135e
出典データセット
uspto-grants-2010_07
特許番号
US07749992B2

関連ノート

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