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

HRID 1297671노트

반응식

HRID 1297671 반응식
[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]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 58585765HCID 58585765, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d85056dfe1184f62b3f864f720d1d264
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250515B2

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