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

HRID 1170103ノート

反応式

HRID 1170103 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+]>C(Cl)CCl>[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 111,2-Dichloroethane溶媒

実験手順

2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde (example 21, step A+B, 150 mg, 0.564 mmol) was dissolved in 5 mL ethylendichloride and acetic acid (136 mg, 2.27 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Sodium triacetoxy borohydride (258 mg, 1.22 mmol) was added and stirring was continued overnight. The reaction mixture was quenched by addition of 50 mL water. The mixture was extracted three times with dichloromethane (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). {2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol was obtained as a light brown solid (105 mg, 69%), MS: m/e=269.5 (M+H+).

後処理

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction mixture was quenched by addition of 50 mL water
  4. extractionThe mixture was extracted three times with dichloromethane (50 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

出典と根拠

ORDレコード
ord-8a8a9a33d10e4478a08016b5919bc33d
出典データセット
uspto-grants-2010_11
特許番号
US07825253B2

反応ノート

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