Bicarbonate Ion → HCID 21192606, compound

HRID 1068034Notes

Reaction equation

HRID 1068034 reaction equation
[N:1]1([CH2:7][C:8]2[CH:32]=[CH:31][C:11]([N:12]([CH:19]=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23]CC)=O)[CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-]>ClCCl>[N:1]1([CH2:7][C:8]2[CH:32]=[C:31]3[C:11](=[CH:10][CH:9]=2)[N:12]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:19]=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]3=[O:23])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 769Bicarbonate IonHCID 21192567HCID 21192567, compound

Product 1

HCID 21192606HCID 21192606, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A flask containing diethyl 2-{[4-(4-morpholinylmethyl)(tetrahydro-2H-pyran-4-yl)anilino]methylene}malonate (0.41 g) is treated with polyphosphoric acid (1.5 g). The reaction mixture is heated to 100° C. under a flow of nitrogen gas. After 1 hour the reaction is cooled to room temperature. The reaction mixture is carefully added to a vigorously stirred mixture of dichloromethane and saturated aqueous bicarbonate. The layers are separated and the basic aqueous layer is extracted with three additional portions of dichloromethane. The combined organic layers are washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane to afford 0.24 g of ethyl 6-(4-morpholinylmethyl)-4-oxo-1-tetrahydro-2H-pyran4-yl-1,4-dihydro-3-quinolinecarboxylate as a tan solid.

Workup

  1. temperatureAfter 1 hour the reaction is cooled to room temperature
  2. customThe layers are separated
  3. extractionthe basic aqueous layer is extracted with three additional portions of dichloromethane
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-a61d44dad73d41319068f403e1e599df
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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