8-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine → 2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol

HRID 598310ノート

反応式

HRID 598310 の反応式
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14](N)[C:13]3[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]([CH3:23])[C:12]=3[C:11]=2[CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:24]([C:21]1[N:22]([CH3:23])[C:12]2[C:11]3[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:20]=1)[CH2:25][CH2:26][CH3:27]

参加物

4

反応物 1

HCID 575453008-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 670510242-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol収率 86.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

A solution of 8-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine (14.65 g, 42.4 mmol), prepared as described in Parts A-C of Example 59, in ethanol (1.2 L) was added to 10% palladium on carbon (6.77 g, 63.6 mmol) and a small amount of ethanol in a Parr vessel. The reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 3.5 hours. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to a small volume. Hexanes were added, and the resulting mixture was allowed to stand overnight in a refrigerator. Crystals formed and were isolated by filtration, washed with hexanes (500 mL), and dried for three days under high vacuum to provide 9.40 g of 2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol as a white solid, mp 219-220.2° C.

後処理

  1. customfor 3.5 hours
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure to a small volume
  5. additionHexanes were added
  6. customCrystals formed
  7. customwere isolated by filtration
  8. washwashed with hexanes (500 mL)
  9. customdried for three days under high vacuum

出典と根拠

ORDレコード
ord-d8197ae05a084777bed4b606cc6ac8ee
出典データセット
uspto-grants-2011_03
特許番号
US07897597B2

反応ノート

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