Dimethylformamide → HCID 59843044, compound

HRID 1878777Notes

Reaction equation

HRID 1878777 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([O:13][CH3:14])=[CH:6]2.CO[C:17]1[CH:18]=N[C:20]2[C:25]([CH:26]=1)=[CH:24][C:23](CO)=[CH:22][CH:21]=2.CS(OS(C)(=O)=O)(=O)=O.C([N:40](CC)CC)C.[Cl-].[Li+].C[N:48]([CH:50]=[O:51])C>>[CH3:14][O:13][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([CH2:2][N:48]1[C:50](=[O:51])[CH:18]=[CH:17][C:26]([C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:40]1)=[CH:12][CH:11]=2

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 433294Lithium ChlorideHCID 59842995HCID 59842995, compoundHCID 598430583-Methoxy-6-quinolinemethanol

Product 1

HCID 59843044HCID 59843044, compound

Procedure

6-(chloromethyl)-3-methoxyquinoline. To a solution of (3-methoxyquinolin-6-yl)methanol (0.17 g, 0.9 mmol) in DMF (10 mL) was added methanesulfonic anhydride (0.4 g, 2 mmol) followed by triethylamine (0.4 ml, 3 mmol). After stirred for 1 h, lithium chloride (0.08 g, 2 mmol) was added. The reaction was continued to stir at rt under N2 for 20 h. The reaction mixture was quenched with water. The resulting mixture was partitioned between EtOAc/sat. NaHCO3 The organic layer was washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, hex:acetone=90%:10%, Flow=30 mL/min). A peak at 30 min was collected. The solvent was removed in vacuo to afford the desired product as white solid (100 mg). MS (ESI pos. ion) m/z (M+1): 208.4. Calc'd exact mass for C11H10ClNO: 207.66. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.96 (s, 3 H) 4.76 (s, 2 H) 7.37 (d, J=2.78 Hz, 1 H) 7.58 (dd, J=8.62, 1.90 Hz, 1 H) 7.75 (s, 1 H) 8.05 (d, J=8.62 Hz, 1 H) 8.69 (d, J=2.92 Hz, 1 H).

Workup

  1. stirringto stir at rt under N2 for 20 h
  2. customThe reaction mixture was quenched with water
  3. customThe resulting mixture was partitioned between EtOAc/
  4. washNaHCO3 The organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified
  8. customA peak at 30 min was collected
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fc5c11299e8e45faaf9fde6c23d0e2fd
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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