Sodium borohydride → 6-Methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-quinoline

HRID 1062584Notes

Reaction equation

HRID 1062584 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:7]=[CH:6]2.[BH4-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 220646106-Methoxy-2-(3-methoxyphenyl)quinoline

Product 1

HCID 220646176-Methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-methoxy-2-(3-methoxy-phenyl)-quinoline (96 mg, 0.36 mmol) in EtOH (3 mL) at 0° C. is added NiCl2.6H2O (86 mg, 0.36 mmol). The reaction mixture is stirred for 30 min before the addition of NaBH4 (55 mg, 1.45 mmol). The mixture is stirred for 16 h while warming to room temperature. An additional portion of NaBH4 (50 mg) is then added and stirring is continued for 3 h. The solvent is removed in vacuo and the resulting residue is partitioned between water and CH2Cl2. The organic phase is washed with water and brine, dried over MgSO4, filtered and concentrated. Flash chromotography (0-50% EtOAc/hexanes) yields 6-methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-quinoline.

Workup

  1. stirringstirring
  2. waitis continued for 3 h
  3. customThe solvent is removed in vacuo
  4. customthe resulting residue is partitioned between water and CH2Cl2
  5. washThe organic phase is washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-059583947d9c4a56b2365766b0eb511a
Source dataset
uspto-grants-2005_11
Patent number
US06962928B2

Reaction notes

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