Bromine → HCID 21387697, compound

HRID 1833840Notes

Reaction equation

HRID 1833840 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][C:7]1[CH2:8][CH2:9][C:10](=[O:13])[NH:11][N:12]=1>C(OCC)(=O)C>[BrH:1].[CH3:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][C:7]1[CH:8]=[CH:9][C:10](=[O:13])[NH:11][N:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 21387665HCID 21387665, compound

Product 1

HCID 21387697HCID 21387697, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of bromine (5.3 ml.) in ethyl acetate (5.3 ml.) was added over 15 minutes to a refluxing solution of 6-(2-methylbenzyl)-2,3,4,5-tetrahydropyridaz-3-one (prepared as described above; 19.2 g.) in ethyl acetate (150 ml.). Heating under reflux was continued for a further 15 minutes. The reaction mixture was then cooled to 0° C. and filtered. Solid 2,3-dihydro-6-(2-methylbenzyl)pyridaz-3-one hydrobromide thus obtained was washed with n-hexane, dried in vacuo, added to an excess of aqueous sodium bicarbonate solution, stirred with a magnetic stirrer for one hour and filtered. The residue was washed with water and dried in air at 60° C. to give 2,3-dihydro-6-(2-methylbenzyl)pyridaz-3-one (13.9 g.) in the form of a fawn coloured powder, m.p. 139°-141° C.

Workup

  1. temperatureHeating
  2. temperatureunder reflux
  3. filtrationfiltered

Sources & evidence

ORD record
ord-07d4605a91554d478f4de299d9d029ad
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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