Glycolic Acid → 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

HRID 1006591노트

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HRID 1006591 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[C:19](OCC)(=[O:21])[CH3:20].S([O-])([O-])(=O)=O.[Mg+2].C(O)(=O)CO>Cl.[Pt]>[CH3:17][CH:16]([CH3:18])[CH2:15][N:14]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[C:20]1[CH2:19][OH:21]

참가 물질

7

반응물 4

HCID 757Glycolic AcidHCID 8857Ethyl AcetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 109993104-Isobutylamino-3-nitroquinoline

생성물 1

HCID 152244061-(2-Methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol수율 89.6%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 313Hydrochloric Acid용매

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온도
155 °C

실험 절차

3-Nitro-4-(2-methylpropylamino)quinoline (36.8 g; 0.15 mol) was added to a mixture of ethyl acetate (300 mL), 5% Pt/C (about 1 g), and magnesium sulfate (30 g). The mixture was hydrogenated at about 50 psi initial pressure. When hydrogenation was complete the solids were filtered from the mixture and the ethyl acetate was evaporated. The resulting intermediate diamine was mixed with glycolic acid (26.9 g; 0.35 mol) and the mixture was heated at 150-160° C. for about 3 hr with occasional manual stirring. The reaction mixture was then dissolved in dilute hydrochloric acid and treated with decolorizing carbon, and the solids were filtered from the mixture. The filtrate was made basic with ammonium hydroxide to precipitate the product as a greenish solid. The solid was filtered and dried to give 34.3 g (89.6%) of crude product. The solid was reprecipitated a second time as above and the product recrystallized from ethyl acetate to give greenish crystals, m.p. 165-168° C. Analysis: Calculated: C, 70.6; H, 6.7; N, 16.5. Found: C, 70.4, H, 6.7; N, 16.3.

후처리

  1. filtrationwere filtered from the mixture
  2. customthe ethyl acetate was evaporated
  3. additiontreated with decolorizing carbon
  4. filtrationthe solids were filtered from the mixture
  5. customto precipitate the product as a greenish solid
  6. filtrationThe solid was filtered
  7. customdried

출처 및 근거

ORD 기록
ord-66a093ee8ca841199948357655f556b2
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790961B2

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