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

HRID 274396노트

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HRID 274396 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d10098f09b04188a27c419d4b6f03fd
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389640

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