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

HRID 2353924

반응식

HRID 2353924 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 722820052-Hydroxyimino-N-indan-5-yl-acetamide수율 81.2%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fc9a7b84854d4c3a840555f158a5135e
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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