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

HRID 1584741Notes

Reaction equation

HRID 1584741 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-afb1c3b5772b48f8afa06e5ff4e24737
Source dataset
uspto-grants-1999_08
Patent number
US05935957

Reaction notes

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