3-Methylpyridine → 7-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580571

反応式

HRID 580571 の反応式
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].N1C=CC=C(C)C=1.[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][NH:30][CH2:29]1>N>[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][N:30]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:29]1

参加物

5

反応物 3

HCID 79703-MethylpyridineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 4583498(4-Methylpyrrolidin-3-yl)methanamine

生成物 1

HCID 139330927-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 21.7%

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

実験手順

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C.

後処理

  1. temperaturewas refluxed for 8.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added dichloromethane-ether (1:3, 37 ml)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with ethanol-ether (1:3)
  6. customrecrystallized from ethanol
  7. customfurther recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

出典と根拠

ORDレコード
ord-f139f10be90c4dafa9e9508b53e7e7e3
出典データセット
uspto-grants-1988_06
特許番号
US04753953

関連ノート

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