7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline → 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2203560ノート

反応式

HRID 2203560 の反応式
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]4[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]4)[C:20]([CH2:30][O:31][CH2:32][CH3:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C(#N)C.C(Cl)(Cl)Cl.CO.[OH-].[Pd+2].[OH-]>[CH3:28][C:25]1([CH3:29])[O:24][CH:23]([CH2:22][N:21]2[C:13]3[C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=4[N:16]=[CH:15][C:14]=3[N:19]=[C:20]2[CH2:30][O:31][CH2:32][CH3:33])[CH2:27][O:26]1

参加物

5

反応物 1

HCID 670511477-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 1363478501-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol収率 93.4%

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 6342Acetonitrile溶媒HCID 21584188Chloroform methanol溶媒

実験手順

Palladium hydroxide (Pearlman's catalyst) (20% wt. % palladium on carbon, 2.2 g) was added to a solution of 7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (22.2 g, 49.6 mmol) in acetonitrile (400 mL) and the reaction mixture was hydrogenated (30 psi, 2.1×105 Pa) for 24 hours on a Parr apparatus. The crude reaction mixture was diluted with 1:1 chloroform/methanol (1 L), then was filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and triturated with acetonitrile. The resulting crystalline material was collected by filtration, washed with acetonitrile, and dried to afford 16.55 g of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol as a white powder, mp 239-240° C.

後処理

  1. customfor 24 hours
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a layer of CELITE filter agent
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customtriturated with acetonitrile
  6. filtrationThe resulting crystalline material was collected by filtration
  7. washwashed with acetonitrile
  8. customdried

出典と根拠

ORDレコード
ord-5b15182092a640f1b7250dacd040ea9a
出典データセット
uspto-grants-2016_06
特許番号
US09365567B2

反応ノート

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