Triethylamine → 3-hydroxy-4-methyl-benzoic acid N'-(4-chloro-benzoyl)-hydrazide

HRID 2081102Notes

Reaction equation

HRID 2081102 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:15]([NH:17][NH2:18])=[O:16].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][NH:17][C:15](=[O:16])[C:14]2[CH:19]=[CH:20][C:21]([CH3:22])=[C:12]([OH:11])[CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 167809363-Hydroxy-4-methylbenzohydrazide

Product 1

HCID 596497183-hydroxy-4-methyl-benzoic acid N'-(4-chloro-benzoyl)-hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-chlorobenzoyl chloride (0.92 mL, 7.22 mmol) (Aldrich), 3-hydroxy-4-methyl-benzoic acid hydrazide (1.0 g, 6.02 mmol) (from Example 6 supra) and triethylamine (1.36 mL) in tetrahydrofuran (20 mL) was heated at 85° C. for 1 day. The reaction mixture was partitioned between ethyl acetate and water. The precipitate washed with ethyl acetate and dichloromethane and dried to give 3-hydroxy-4-methyl-benzoic acid N′-(4-chloro-benzoyl)-hydrazide. (Yield 1.28 g, 70%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe precipitate washed with ethyl acetate and dichloromethane
  3. customdried

Sources & evidence

ORD record
ord-0e7478dd2fd64bbb906cee4406f72f25
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

Loading…