Formaldehyde → HCID 20074934、化合物

HRID 1709730ノート

反応式

HRID 1709730 の反応式
[C:1]([C:4]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:9][CH2:8][CH2:7][N:6]3[N:5]=1)(=[O:3])[CH3:2].[CH2:16]=O.[Cl-:18].[CH3:19][NH2+:20][CH3:21]>C(O)(=O)C>[ClH:18].[N:5]1[N:6]2[C:15]3[C:10]([CH2:9][CH2:8][CH2:7]2)=[CH:11][CH:12]=[CH:13][C:14]=3[C:4]=1[C:1](=[O:3])[CH2:2][CH2:19][N:20]([CH3:16])[CH3:21]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 12954980Dimethylazanium;chlorideHCID 20074920HCID 20074920、化合物

生成物 1

HCID 20074934HCID 20074934、化合物収率 35%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

1.5 g (7.5 mmol) of 2-acetyl-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline together with 0.45 g (15 mmol) of paraformaldehyde and 1.35 g (16 mmol) of dimethylammonium chloride in 50 ml of acetic acid was stirred for 2 hours at 100° C. The mixture was evaporated in vacuum, and the residue was shaken with a mixture of methylene chloride and sodium hydroxide solution. The organic layer was washed with saline and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/methanol/ammonia (92.5/7/0.5) as an eluent. The desired fractions were evaporated in vacuum, and the residue was dissolved in alcoholic hydrochloric acid. 0.76 g (35%) of 1-(7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-yl)-3-(N,N-dimethylamino)-propan-1-one hydrochloride were obtained after evaporating in vacuum. This product (0.76 g, 2.6 mmol) was boiled for 18 hours together with 1 g (12 mmol) of 2-methyl-imidazole in a mixture of 20 ml of water and 5 ml of propanol-1. The mixture was diluted with 2N sodium hydroxide and extracted with methylene chloride. The organic layer was separated and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/methanol/ammonia (92.5/7/0.5) as an eluent. 0.5 g (69%) of the desired product were obtained; melting point 133°-134° C. 13C NMR (CDCl3, Ref.: TMS):

後処理

  1. customThe mixture was evaporated in vacuum
  2. washThe organic layer was washed with saline
  3. customevaporated in vacuum
  4. customThe residue was chromatographed
  5. customThe desired fractions were evaporated in vacuum
  6. dissolutionthe residue was dissolved in alcoholic hydrochloric acid

出典と根拠

ORDレコード
ord-57e7ddff41d54a1e845673dac435c948
出典データセット
uspto-grants-1990_08
特許番号
US04950759

反応ノート

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