Toluene → HCID 23336376, compound

HRID 903546Notes

Reaction equation

HRID 903546 reaction equation
[NH:1]([CH2:3][CH:4]([OH:8])[CH:5]([CH3:7])[CH3:6])[NH2:2].[Cl:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([CH2:16][CH2:17][C:18](O)=[O:19])=O)=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>O>[OH:8][CH:4]([CH:5]([CH3:7])[CH3:6])[CH2:3][N:1]1[C:18](=[O:19])[CH2:17][CH2:16][C:14]([C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:22][CH:21]=2)=[N:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 776043-(4-Chlorobenzoyl)propionic acidHCID 23336377HCID 23336377, compound

Product 1

HCID 23336376HCID 23336376, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 9.5 grams (0.085 mol) of 1-hydrazino-3-methyl-2-butanol, 14.4 grams (0.070 mol) of 3-(p-chlorobenzoyl)-propanoic acid and 100 milliliters of toluene are stirred in a flask equipped with a condenser and Dean-Stark water collecting apparatus at reflux for about 2.0 hours during which 2.8 milliliters of water is collected in the Dean-Stark tube. The toluene solution is washed with 50 milliliters of 2 N sodium hydroxide solution, 25 ml. of 2 N hydrochloric acid and then water. The toluene layer is then dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. The solid obtained is crystallized from methylene chloride-petroleum ether to yield 19.0 grams of 2-(2-hydroxy-3-methylbutyl)-6-(p-chlorophenyl)4,5-dihydropyridazine-3(2H)-one, (m.p. 90°-92° C.)

Workup

  1. customequipped with a condenser
  2. customis collected in the Dean-Stark tube
  3. washThe toluene solution is washed with 50 milliliters of 2 N sodium hydroxide solution, 25 ml
  4. dry with materialThe toluene layer is then dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe solid obtained
  8. customis crystallized from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-0a40f5a3999c4eb69d81e87e8b75fe24
Source dataset
uspto-grants-1980_10
Patent number
US04228166

Reaction notes

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