Dimethylformamide → Methyl 3-benzyloxy-6-ethoxypicolinate

HRID 274881Notes

Reaction equation

HRID 274881 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([OH:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20](Br)[CH3:21].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([O:15][CH2:20][CH3:21])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 178499129HCID 178499129, compound

Product 1

HCID 20088901Methyl 3-benzyloxy-6-ethoxypicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (19 mmol) of methyl 3-benzyloxy-6-hydroxypicolinate, 2.1 g (19 mmol) of ethyl bromide and 2.9 g (21 mmol) of potassium carbonate were added to 100 ml of DMF, and the resultant mixture was reacted at 80° C. for 5 hours. After the reaction, the reaction content was poured into water, and was extracted with ethyl acetate, washed with water, dried and concentrated. The residue thus obtained was purified by column chromatography to obtain an aimed compound.

Workup

  1. customAfter the reaction
  2. extractionwas extracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6480cc74b20c4b78935446d42d05cad2
Source dataset
uspto-grants-1995_02
Patent number
US05391537

Reaction notes

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