Sodium Bicarbonate → N-methyl-N-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methyl)-5,6,7,8-tetrahydroquinolin-8-amine

HRID 628694Notes

Reaction equation

HRID 628694 reaction equation
[CH3:1][NH:2][CH:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.[CH3:13][N:14]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:17][N:16]=[C:15]1[CH:25]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CC(O)=O>[CH3:1][N:2]([CH2:25][C:15]1[N:14]([CH3:13])[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:17][N:16]=1)[CH:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 115428934-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehydeHCID 58985336N-methyl-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 44242330N-methyl-N-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methyl)-5,6,7,8-tetrahydroquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-methyl-5,6,7,8-tetrahydroquinolin-8-amine, 5, (0.39 g, 2.40 mmol) in 1,2-dichloroethane (4 mL) was added 4-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehyde, 36, (0.41 g, 2.20 mmol), sodium triacetoxyborohydride (0.84 g, 3.90 mmol), and AcOH (1 drop). The reaction mixture was heated to 65° C. and stirred for 18 h. The reaction mixture was cooled to room temperature, poured into saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic phases were washed with brine then dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified via chromatography on basic alumina (0-5% methanol/dichloromethane) yielding BP: 1H NMR (400 MHz, CDCl3) δ 8.39, (d, J=4.8 Hz, 1H), 7.58-7.53 (m, 2H), 7.46-7.39, (m, 3H), 7.32, (d, J=8.4 Hz, 1H), 7.01, (dd, J=7.2, 4.4 Hz, 1H), 4.04-3.92, (m, 2H), 3.78, (d, J=14.0 Hz, 1H), 2.85-2.74, (m, 1H), 2.71-2.62 (m, 1H), 3.33, (s, 3H), 2.12-1.94 (m, 3H), 1.74-1.62 (m, 1H); ESI+ MS: m/z (rel intensity) 334 (100, M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via chromatography on basic alumina (0-5% methanol/dichloromethane)
  8. customyielding BP

Sources & evidence

ORD record
ord-bdb17e4abab741b5815050b095b0650c
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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