Hydrochloric Acid → 6-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile

HRID 1297671ノート

反応式

HRID 1297671 の反応式
[BH4-].[Li+].C([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]#[N:19])=[C:11]2[CH2:20][CH:21]([CH3:23])[CH3:22])=O)C.Cl>CCOCC.CO.O>[OH:5][CH2:6][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]([C:18]#[N:19])[CH:11]2[CH2:20][CH:21]([CH3:23])[CH3:22]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 58585765HCID 58585765、化合物

生成物 1

HCID 585857716-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile収率 43.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To the suspension of lithium borohydride (93 mg, 4.3 mmol) and methanol (170 uL, 4.3 mmol) in ether (20 mL) was added the solution of 3-cyano-4-isobutyl-quinoline-6-carboxylic acid ethyl ester (example 46d, 600 mg, 2.1 mmol) in ether (5 mL). The mixture was stirred at reflux overnight. The mixture of water and methanol (v/v 1:1, 40 mL) was added to the above solution. Then 1 N HCl (3 mL) was added to quench the reaction. The product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 5%-50% ethyl acetate in hexanes in 50 min) afforded 6-hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile (220 mg, 43%) as a yellow solid. LC-MS m/e 243 (MH+).

後処理

  1. temperatureat reflux overnight
  2. additionwas added to the above solution
  3. customto quench
  4. customthe reaction
  5. extractionThe product was extracted with ethylacetate
  6. washThe combined organic layers were successively washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d85056dfe1184f62b3f864f720d1d264
出典データセット
uspto-grants-2007_07
特許番号
US07250515B2

反応ノート

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