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

HRID 396983ノート

反応式

HRID 396983 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 0.2 N 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. Analysis: Calculated: %C, 67.3; %H, 6.7; %N, 14.7; Found: %C, 67.2; %H, 6.6; %N, 14.6.

後処理

  1. extractionThe ethyl acetate solution was extracted twice with 0.2 N 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-13071fdee6d348a1959ac75f673dd97f
出典データセット
uspto-grants-2003_08
特許番号
US06608201B2

反応ノート

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