Sodium Carbonate → 4-[(3-Chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile

HRID 47348ノート

反応式

HRID 47348 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)=[N:9][N:8]=1.Cl.[CH3:32][O:33][NH2:34].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:20][CH2:21][C:22](=[N:34][O:33][CH3:32])[CH2:23][CH2:24]2)=[N:9][N:8]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 105040684-(3-Chloro-4-methoxy-benzylamino)-1-(4-oxo-piperidin-1-yl)-phthalazine-6-carbonitrile; hydrochloride

生成物 1

HCID 227444584-[(3-Chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile収率 48.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1.19 g 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-oxopiperidino]-6-phthalazine carbonitrile, 354 mg methoxyamine hydrochloride, 1.2 g sodium carbonate, and 10 ml ethanol was heated under reflux for 2 hr. After cooling, saline was added to the reaction solution which was then extracted with ethyl acetate. It was dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was purified by silica gel column chromatography to give 620 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazine carbonitrile. This product was dissolved in a mixed solvent of methanol and ethanol, and recrystallized by adding 0.35 ml of 4 N hydrochloric acid/ethyl acetate to give 388 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-[4-(methoxyimino)piperidino]-6-phthalazinecarbonitrile hydrochloride.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. temperatureAfter cooling
  4. additionsaline was added to the reaction solution which
  5. extractionwas then extracted with ethyl acetate
  6. dry with materialIt was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fe397180f11f4113be6e005dcd113628
出典データセット
uspto-grants-2004_03
特許番号
US06699870B2

反応ノート

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