Methanol → 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3carboxaldehyde O-methyl oxime

HRID 867560

반응식

HRID 867560 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][NH2:23].C(=O)(O)[O-].[Na+].CO>O>[CH3:21][O:22][N:23]=[CH:16][C:15]1[N:14]=[CH:13][N:12]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=3[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]=12

참가 물질

6

반응물 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 198515847-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

생성물 1

HCID 867424647-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3carboxaldehyde O-methyl oxime

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

A suspension of 5.51 g (20 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde, 2.23 g (26.6 mmol) of O-methylhydroxylamine hydrochloride and 75 ml of water is treated dropwise at room temperature with a solution of 7.67 g (26.6 mmol) of sodium bicarbonate in 65 ml of water. 40 ml of methanol are added thereto and the mixture is stirred at 70° for 8 hours. The mixture is then poured into 700 ml of water, the suspension is suction filtered and the filter residue is dissolved in methylene chloride. The solution is dried over magnesium sulphate and evaported. By chromatography on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate there is obtained 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3carboxaldehyde O-methyl oxime of melting point 173°-174°.

후처리

  1. filtrationsuction filtered
  2. dissolutionthe filter residue is dissolved in methylene chloride
  3. dry with materialThe solution is dried over magnesium sulphate
  4. washBy chromatography on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-06f8a37e3e1a48a6bb608e40d866fe64
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04775671

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