Ethyl orthopropionate → 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol

HRID 2404992ノート

反応式

HRID 2404992 の反応式
[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].Cl.N1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:30]=1[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])=[CH:28][CH:27]=[CH:26][CH:25]=2>N1C=CC=CC=1>[CH2:2]([C:3]1[N:31]([CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:20]=1)[CH3:1]

参加物

5

反応物 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 689990994-[(3-Aminoquinolin-4-yl)amino]butan-1-ol

生成物 1

HCID 689965274-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Triethyl orthopropionate (15.1 mL of 97%, 1.1 eq.) and a catalytic amount of pyridine hydrochloride were added to a solution of 4-[(3-aminoquinolin-4-yl)amino]butan-1-ol (16 g, 69 mmol, 1 eq.) in pyridine (150 mL). The reaction mixture was refluxed for 1 hour at which time analysis by TLC indicated that all of the starting material had been consumed. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water (300 mL). The resulting solid was isolated by filtration and then recrystallized from ethyl acetate to provide 8.2 g of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol. A second crop (1.9 g) was obtained by reducing the volume of the mother liquor.

後処理

  1. temperatureThe reaction mixture was refluxed for 1 hour at which time analysis by TLC
  2. customhad been consumed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was triturated with water (300 mL)
  5. customThe resulting solid was isolated by filtration
  6. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-337870e936424f2d9f984e592e2cbea5
出典データセット
uspto-grants-2014_08
特許番号
US08802853B2

反応ノート

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