Diazomethane → Methyl 8-Hydroxyquinoline-2-Carboxylate

HRID 2393091Notes

Reaction equation

HRID 2393091 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7]2.[N+](=[CH2:17])=[N-]>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:17])=[O:13])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 740798-Hydroxyquinaldic acid

Product 1

HCID 12336161Methyl 8-Hydroxyquinoline-2-CarboxylateYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Hydroxyquinoline-2-carboxylic acid (2.08 g) and tetrahydrofuran (200 ml) were combined and stirred with ice bath cooling. Diazomethane (approx. 16.6 mmol in solution in diethyl ether) was then added and the whole stirred for 1.5 h as it slowly warmed to room temperature. Nitrogen was blown through the reaction mixture to purge any excess diazomethane and the solution was evaporated in vacuo to give the title compound (1.6 g).

Workup

  1. temperaturecooling
  2. stirringthe whole stirred for 1.5 h as it
  3. customto purge any excess diazomethane
  4. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-4c7b361eae324ebeabfcce85d7c21218
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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