Triethylamine → 3-hydroxy-4-methyl-benzoic acid N'-[2-(4-chloro-phenyl)-acetyl]-hydrazide

HRID 2081097Notes

Reaction equation

HRID 2081097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:16]([NH:18][NH2:19])=[O:17].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:19][NH:18][C:16](=[O:17])[C:15]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:13]([OH:12])[CH:14]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 167809363-Hydroxy-4-methylbenzohydrazide

Product 1

HCID 596497123-hydroxy-4-methyl-benzoic acid N'-[2-(4-chloro-phenyl)-acetyl]-hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-chlorophenylacetyl chloride (1.36 g, 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 aqueous phase was extracted with ethyl acetate (1×). The combined organic phase washed with water and brine, dried (magnesium sulfate) and concentrated. The residue washed with ethyl acetate and dichloromethane and dried to give 3-hydroxy-4-methyl-benzoic acid N′-[2-(4-chloro-phenyl)-acetyl]-hydrazide. (Yield 0.91 g, 95%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate (1×)
  3. washThe combined organic phase washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. washThe residue washed with ethyl acetate and dichloromethane
  7. customdried

Sources & evidence

ORD record
ord-d0a67b923bab47f98c9be80e596f0423
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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