Dimethylformamide → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde

HRID 1481677

Reaction equation

HRID 1481677 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.O=P(Cl)(Cl)Cl.CN([CH:20]=[O:21])C>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH:20]=[O:21])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 681091,2,3,4-Tetrahydro-1-methylquinoline

Product 1

HCID 27930141-Methyl-1,2,3,4-tetrahydroquinoline-6-carbaldehydeYield 41%

Procedure

To a solution of 1-methyl-1,2,3,4-tetrahydroquinoline (4.4 g, ca. 30.0 mmol) in DMF (30 mL) was added POCl3 (2.8 mL, 30.0 mmol, 1.0 eq) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice then extracted with Et2O (3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-20% EtOAc in hexanes) to afford the title compound (2.17 g, 12.4 mmol, 41% over two steps).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthen extracted with Et2O (3×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationthen concentrated
  5. customto give a crude product which
  6. customwas purified by flash column chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-07b44852b8e0464cbdcdb3079587b4e9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Linked notes

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