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

HRID 856959Notes

Reaction equation

HRID 856959 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7fb215145b734a3a90d6e1caef304025
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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