Pyridine → HCID 58118641, compound

HRID 1690795Notes

Reaction equation

HRID 1690795 reaction equation
[I-].[Li+].[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH:10]([C:15]([O:17]C)=[O:16])[CH2:9][CH2:8][C:7]=2[N:6]=1)#[N:4].N1C=CC=CC=1>>[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH:10]([C:15]([OH:17])=[O:16])[CH2:9][CH2:8][C:7]=2[N:6]=1)#[N:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 58118601HCID 58118601, compound

Product 1

HCID 58118641HCID 58118641, compoundYield 82%

Procedure

A mixture of lithium iodide (10.3 g, 77.0 mmol), methyl 2-cyano-5,6,7,8-tetrahydroquinoline-6-carboxylate (3.32 g, 15.4 mmol) and pyridine (39 mL, 480 mmol) was divided evenly between two 35 mL vials and the mixtures submitted to microwave irradiation for 4 hr at 130° C. The reactions were combined and concentrated to ˜15 mL. The residue was diluted with water (50 mL) and DCM (200 mL) and 1M citric acid (150 mL) was added until a pH of 4 was attained. The aqueous was extracted with additional DCM (200 mL) and the combined organics was washed with 0.25 M citric acid (150 mL). The citric acid wash was back extracted with DCM (50 mL) and the combined organics were dried ((Na2SO4), filtered and evaporated. The residue was dissolved in DCM (200 mL) and washed with 0.5 M citric acid (50 mL×2). Each citric acid wash was back extracted with DCM (25 mL) and the combined organics dried (Na2SO4), filtered and evaporated to obtain a yellow solid (2.54 g, 82%). m/z=201.2 (M−H)−. 1H NMR (400 MHz, DMSO-d6) δ 12.47 (br s, 1H), 7.80 (d, J=8.1 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 3.12-2.84 (m, 4H), 2.83-2.74 (m, 1H), 2.22-2.13 (m, 1H), 1.94-1.83 (m, 1H).

Workup

  1. customirradiation for 4 hr at 130° C
  2. concentrationconcentrated to ˜15 mL
  3. additionThe residue was diluted with water (50 mL) and DCM (200 mL) and 1M citric acid (150 mL)
  4. additionwas added until a pH of 4
  5. extractionThe aqueous was extracted with additional DCM (200 mL)
  6. washthe combined organics was washed with 0.25 M citric acid (150 mL)
  7. washThe citric acid wash
  8. extractionwas back extracted with DCM (50 mL)
  9. dry with materialthe combined organics were dried ((Na2SO4)
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residue was dissolved in DCM (200 mL)
  13. washwashed with 0.5 M citric acid (50 mL×2)
  14. washEach citric acid wash
  15. extractionwas back extracted with DCM (25 mL)
  16. dry with materialthe combined organics dried (Na2SO4)
  17. filtrationfiltered
  18. customevaporated

Sources & evidence

ORD record
ord-0cb94e115ebb460a826dd621e3d21649
Source dataset
uspto-grants-2012_04
Patent number
US08153651B2

Reaction notes

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