Formaldehyde → 1-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde

HRID 856959노트

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HRID 856959 반응식
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Mg+2].[Cl-].C(N(CC)CC)C.[CH2:29]=[O:30].[Cl-].[NH4+]>C(#N)C.O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:29]=[O:30])=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 218649361-Benzyl-1,2,3,4-tetrahydroquinolin-7-ol

생성물 1

HCID 218649621-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde수율 15.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-benzyl-1,2,3,4-tetrahydro-quinolin-7-ol (297 mg, 1.24 mmol) from step 2 in anhydrous acetonitrile (6 mL) was added magnesium chloride (177 mg, 1.86 mmol), triethylamine (650 μl, 4.65 mmol) and paraformaldehyde (251 mg, 8.38 mmol). The reaction mixture was reflux for a half hour. Added some water and saturated aqueous ammonium chloride until pH=7. Extracted it with ether several times. The organic layer was combined, dried over magnesium sulfate, and filtrated. The solution was evaporated under vacuum. The crude residue was purified by prep TLC eluting with 25% ethyl acetate-hexane and providing 50 mg (15%) of the title compound. 1H-NMR (CDCl3) δ 11.4 (s, 1H), 9.38 (s, 1H), 7.30–7.20 (m, 3H), 7.14–7.10 (m, 2H), 6.94 (s, 1H), 5.93 (s, 1H), 4.48 (s, 2H), 3.36 (t, J=5.5 Hz, 2H), 2.68 (t, J=6.2 Hz, 2H), 1.93 (m, 2H); MS LC-MS (MH+=268.5), LC MS RT: 3.24 min.

후처리

  1. temperatureThe reaction mixture was reflux for a half hour
  2. extractionExtracted it with ether several times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customThe solution was evaporated under vacuum
  6. customThe crude residue was purified by prep TLC
  7. washeluting with 25% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-7fb215145b734a3a90d6e1caef304025
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144885B2

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