Pyridine → Ethyl 3-(4-carboxy-2-methylphenylhydrazono)-4-oxopentanoate

HRID 2292635Notes

Reaction equation

HRID 2292635 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].N([O-])=O.[Na+].[C:16]([CH:19](C(=O)C)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])[CH3:17].[N:29]1C=CC=CC=1>O.C(O)C.Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][N:29]=[C:19]([C:16](=[O:18])[CH3:17])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:3]([CH3:11])[CH:4]=1)([OH:8])=[O:7]

Participants

8

Reactant 4

HCID 1049PyridineHCID 755984-Amino-3-methylbenzoic acidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 23668193Sodium Nitrite

Product 1

HCID 86751496Ethyl 3-(4-carboxy-2-methylphenylhydrazono)-4-oxopentanoate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

A mixture of 3 g (19.8 mmol) of 4-amino-3-methylbenzoic acid in 50 ml of water and 50 ml of ethanol and 3.56 ml of concentrated hydrochloric acid was cooled in an ice bath and then 1.5 g of NaNO2 (21.8 mmol) in 10 ml of water was added portionwise. The mixture was allowed to come to room temperature and then added to a solution of 4.06 g (21.8 mmol) of ethyl 3-acetyl-4-oxopentanoate and 8 ml of pyridine in 25 ml of ethanol. The reaction mixture was left for 24 hr at room temperature with stirring. The mixture was acidified with concentrated hydrochloric acid and the mixture diluted with 20 ml of water. The resulting solid was collected and washed with water and pentane to yield 5.2 g of ethyl 3-(4-carboxy-2-methylphenylhydrazono)-4-oxopentanoate with m.p. 161°-162.5° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. customto come to room temperature
  3. customThe resulting solid was collected
  4. washwashed with water and pentane

Sources & evidence

ORD record
ord-c00576b04f1c4997b885d644cc60d1bd
Source dataset
uspto-grants-1997_11
Patent number
US05684024

Reaction notes

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