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

HRID 131175ノート

反応式

HRID 131175 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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); MS LC-MS (MH+=268.5), LC MS RT: 3.24 min.

後処理

  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

出典と根拠

ORDレコード
ord-d1493bfb0f8547efbe47251674d23577
出典データセット
uspto-grants-2008_06
特許番号
US07384947B2

反応ノート

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