Acetic Acid → 2-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

HRID 1453541Notes

Reaction equation

HRID 1453541 reaction equation
O.[NH2:2][NH2:3].[Br:4][C:5]1[N:9]([CH2:10][C:11]#[C:12][CH3:13])[C:8]([C:14]([O:16]C)=O)=[C:7]([CH:18]=O)[N:6]=1.C(O)(=O)C>C(O)C>[Br:4][C:5]1[N:9]([CH2:10][C:11]#[C:12][CH3:13])[C:8]2[C:14](=[O:16])[NH:3][N:2]=[CH:18][C:7]=2[N:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 21947682methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

Product 1

HCID 219476582-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.31 ml hydrazine hydrate, dissolved in 1 ml of ethanol, are added dropwise at ambient temperature to a solution of 1.80 g methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate in 25 ml of ethanol. Five minutes later 1.5 ml concentrated acetic acid are added, and the mixture is refluxed for 30 minutes. After cooling the solid precipitate is suction filtered, washed with 10 ml of ethanol and 20 ml diethyl ether and dried.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperatureAfter cooling the solid precipitate
  3. filtrationfiltered
  4. washwashed with 10 ml of ethanol and 20 ml diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-ffab164789b1442abc1cb1d0c5c08b75
Source dataset
uspto-grants-2009_01
Patent number
US07476671B2

Reaction notes

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