Triethylamine → HCID 19081211, compound

HRID 963480Notes

Reaction equation

HRID 963480 reaction equation
[CH3:1][C:2]1[N+:10]([O-:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH2:27]([N:29](CC)[CH2:30][CH3:31])[CH3:28].N1CCCC1>ClCCl>[N:29]1([C:4]([C:3]2[C:2]([CH3:1])=[N+:10]([O-:11])[CH:9]=[CH:8][CH:7]=2)=[O:6])[CH2:30][CH2:31][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 190812032-Methyl-1-oxo-1lambda~5~-pyridine-3-carboxylic acid

Product 1

HCID 19081211HCID 19081211, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 2-methylnicotinic acid-1-oxide (0.701 g) and N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (1.243 g) in dichloromethane (30 ml) was added dropwise a solution of triethylamine (0.570 g) in dichloromethane (5 ml) and followed a solution of pyrrolidine (0.407 g) in dichloromethane (5 ml) under stirring at cooling in an ice-bath. After completion of the addition, the mixture was allowed to stand to room temperature overnight. The reaction mixture was washed with water and dried over sodium sulfate. Removal of the solvent gave a crude product. The crude product was purified by column chromatography on silica gel with a mixture of chloroform and methanol (50:1) as an elunet to give 3-(1-pyrrolidinylcarbonyl)-2-methylpyridine-1-oxide (0.530 g).

Workup

  1. temperatureat cooling in an ice-bath
  2. additionAfter completion of the addition
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent
  6. customgave a crude product
  7. customThe crude product was purified by column chromatography on silica gel with a mixture of chloroform and methanol (50:1) as an elunet

Sources & evidence

ORD record
ord-64f439e993a644b5bab9bf14d82d8cf4
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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