3-Pyridinemethanol → HCID 59737448, compound

HRID 1907727Notes

Reaction equation

HRID 1907727 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[NH:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([O:25][CH3:26])=[O:24])=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](CO)[CH:28]=1>C(Cl)Cl>[N:13]1([C:5]([O:6][CH2:7][C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)=[O:11])[C:22]2[C:17](=[CH:18][C:19]([C:23]([O:25][CH3:26])=[O:24])=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 94429TriphosgeneHCID 16740570Methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 59737448HCID 59737448, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphosgene (0.489 g, 1.61 mmol) in DCM (5 mL) was treated with compound 212 (0.286 g, 1.50 mmol) and the solution was stirred under N2 atmosphere at room temperature for 18 h. The DCM was removed under reduced pressure, the residue was dissolved in pyridin-3-yl methanol (1.0 mL, 10.3 mmol) and the solution was stirred at room temperature for 8 h then diluted with DCM, washed with saturated NaHCO3, H2O, dried over MgSO4, filtered and concentrated to give title compound 213 (0.527 g, 100% yield).

Workup

  1. customThe DCM was removed under reduced pressure
  2. stirringthe solution was stirred at room temperature for 8 h
  3. washwashed with saturated NaHCO3, H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-396743c8e25042ed86b901c9e4bf8fa5
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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