Acetic Acid → {2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

HRID 1669719ノート

反応式

HRID 1669719 の反応式
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([CH:19]=[O:20])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][OH:20])[N:10]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866194932-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde

生成物 1

HCID 44218152{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde (150 mg, 0.56 mmol) was dissolved in 5 mL dichloroethan. Acetic acid (136 mg, 2.3 mmol) and sodium triacetoxy borohydride (258 mg, 1.2 mmol) were added. The reaction mixture was stirred at room temperature overnight and quenched by addition of 2N sodium carbonate solution (50 mL). The mixture was extracted three times with ethyl acetate (100 mL each). The organic phases were pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a light brown solid (105 mg, 69%), MS: m/e=269.5 (M+H+).

後処理

  1. customquenched by addition of 2N sodium carbonate solution (50 mL)
  2. extractionThe mixture was extracted three times with ethyl acetate (100 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->50:50 gradient)

出典と根拠

ORDレコード
ord-e635a2a9f43f464a90b0ecf7c801b485
出典データセット
uspto-grants-2011_08
特許番号
US07989628B2

反応ノート

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