Methoxyacetic Acid → alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 274396

反応式

HRID 274396 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][CH2:20][C:21](O)=O>C(OCC)(=O)C>[CH3:16][C:14]([CH3:15])([OH:17])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:21]1[CH2:20][O:19][CH3:18]

参加物

4

反応物 2

HCID 12251Methoxyacetic AcidHCID 149869411-((3-Aminoquinolin-4-yl)amino)-2-methylpropan-2-ol

生成物 1

HCID 15224447alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol収率 9.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
170 °C

実験手順

3-Amino-4-(2-hydroxy-2-methylpropylamino)quinoline (7.5 g, 32 mmol) was combined with methoxyacetic acid (7.5 mL, 97 mmol) and heated at about 170° C. for about 3 hours. The resulting solid residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was extracted twice with 0.2N sodium hydroxide, washed with water, dried over magnesium sulfate, treated with activated charcoal and then concentrated to a volume of about 50 mL. Hexane was added to the ethyl acetate and the resulting precipitate was collected and dried to provide 0.9 g of the desired product as a crystalline solid, m.p. 145°-148° C.

後処理

  1. extractionThe ethyl acetate solution was extracted twice with 0.2N sodium hydroxide
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with activated charcoal
  5. concentrationconcentrated to a volume of about 50 mL
  6. additionHexane was added to the ethyl acetate
  7. customthe resulting precipitate was collected
  8. customdried

出典と根拠

ORDレコード
ord-3d10098f09b04188a27c419d4b6f03fd
出典データセット
uspto-grants-1995_02
特許番号
US05389640

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