Diazomethane → HCID 178497913, compound

HRID 487064Notes

Reaction equation

HRID 487064 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][C:5]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]>CCOCC.C1COCC1>[OH:4][C:5]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:3])=[O:8]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 178425908HCID 178425908, compound

Product 1

HCID 178497913HCID 178497913, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Excess diazomethane in ether was added portionwise over 15 mins to 9.58 g (~60 mmoles) of 2-hydroxy-6-methyl nicotinic acid in 900 mL of THF at 0°. After stirring 2 hours, excess diazomethane was removed in vacuo. The resulting white solid was filtered and washed with hexane and dried. This fluffy solid was the required methyl ester. The filtrate was concentrated. The resulting solid was redissolved in a minimum amount of THF and hexane was added until no further precipitation was observed. Solid was filtered and washed with hexane and dried to provide more of the desired compound.

Workup

  1. customexcess diazomethane was removed in vacuo
  2. filtrationThe resulting white solid was filtered
  3. washwashed with hexane
  4. customdried
  5. concentrationThe filtrate was concentrated
  6. dissolutionThe resulting solid was redissolved in a minimum amount of THF and hexane
  7. additionwas added until no further precipitation
  8. filtrationSolid was filtered
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-081eee156929442594546633c0e75235
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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