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

HRID 1601660ノート

反応式

HRID 1601660 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 313Hydrochloric Acid溶媒

反応条件

温度
155 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e2f22d54eef4b46a5ab648ccafb86d3
出典データセット
uspto-grants-1999_11
特許番号
US05977366

反応ノート

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