Sulfuric Acid → Dimethyl 5-(2-chloroethyl)-6-chloro-2,3-pyridinedicarboxylate

HRID 1741628Notes

Reaction equation

HRID 1741628 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][CH2:13][Cl:14])=[CH:10][C:9]2[C:4](=[C:5]([O:17][CH3:18])C=CC=2OC)[N:3]=1.CO[CH:21]([O:24]C)[O:22][CH3:23].S(=O)(=O)(O)[OH:27].O=[O+][O-]>CO>[Cl:1][C:2]1[N:3]=[C:4]([C:5]([O:17][CH3:18])=[O:27])[C:9]([C:21]([O:22][CH3:23])=[O:24])=[CH:10][C:11]=1[CH2:12][CH2:13][Cl:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 24823OzoneHCID 19010371HCID 19010371, compound

Product 1

HCID 19958230Dimethyl 5-(2-chloroethyl)-6-chloro-2,3-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-3-(2-chloroethyl)-5,8-dimethoxyquinoline (22.0 g, 0.077 mole) in 1 L methanol containing 80 mL of trimethylorthoformate and 2 mL concentrated sulfuric acid is stirred at room temperature while ozone is bubbled in until TLC indicates the disappearance of starting material. The reaction is concentrated in vacuo, and the residue is partitioned between ether and saturated aqueous bicarbonate. The organic layer is washed further with bicarbonate, then with aqueous bisulfite. Drying and concentration in vacuo affords the desired product as an oil.

Workup

  1. customis bubbled in until TLC
  2. concentrationThe reaction is concentrated in vacuo
  3. customthe residue is partitioned between ether and saturated aqueous bicarbonate
  4. washThe organic layer is washed further with bicarbonate
  5. customDrying
  6. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-7590399d07784ef4b06b64c6387cea8a
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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