Hydrochloric Acid → Ethyl 3-(4-carboxy-2-methylphenylhydrazono)-4-oxopentanoate

HRID 650226

Reaction equation

HRID 650226 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].Cl.[N:13]([O-])=O.[Na+].[C:17]([CH:20](C(=O)C)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:19])[CH3:18]>O.C(O)C.N1C=CC=CC=1>[CH3:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:1][N:13]=[C:20]([C:17](=[O:19])[CH3:18])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:6]([OH:8])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 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 702EthanolSolvent2×HCID 962WaterSolvent3×HCID 1049PyridineSolvent

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 hours at room temperature with stirring. The mixture was acidified with concentrated hydrochloric acid and diluted with 20 ml. of water. The resulting solid was collected and washed with water and pentane to yield 5.2 g.

Workup

  1. additionA mixture of 3 g
  2. customto come to room temperature
  3. additionadded to a solution of 4.06 g
  4. additiondiluted with 20 ml
  5. customThe resulting solid was collected
  6. washwashed with water and pentane
  7. customto yield 5.2 g

Sources & evidence

ORD record
ord-2546c1a8b1344d09ab0e853e19191ade
Source dataset
uspto-grants-2001_08
Patent number
US06271373B1

Linked notes

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