Acetic Acid → Methyl 2-chloro-2-(2-(2-(2-cyanoethoxy)phenyl)hydrazono)acetate

HRID 1629120Notes

Reaction equation

HRID 1629120 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH2:6][C:7]#[N:8].C(O)(=O)C.[N:17]([O-])=O.[Na+].[CH3:21][O:22][C:23](=[O:29])[CH:24]([Cl:28])C(C)=O>Cl.O>[Cl:28][C:24](=[N:17][NH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH2:6][C:7]#[N:8])[C:23]([O:22][CH3:21])=[O:29]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 107332Methyl 2-chloroacetoacetateHCID 23668193Sodium NitriteHCID 61028432HCID 61028432, compound

Product 1

HCID 86711716Methyl 2-chloro-2-(2-(2-(2-cyanoethoxy)phenyl)hydrazono)acetate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To aniline 84 (1.65 g, 10.2 mmol) in acetic acid (6.80 mL, 120 mmol) and 2 M of Hydrogen chloride in water (13.59 mL), then sodium nitrite (1.0290 g, 14.914 mmol;) was added while stirring vigorously at 0° C. (FIG. 18). After 20 minutes, 2-chloroacetoacetate methyl ester (1.5317 g, 10.173 mmol) was added dropwise via syringe and the mixture was warmed to room temperature over 5 hours. Then, the organic layer was extracted twice with 100 mL diethyl ether and dried with sodium sulfate, and concentrated. The crude product 85 was taken forward for next step. LRMS m/z Calcd. for C12H12ClN3O3 : 281.05672, found: 282.1 [M+1].

Workup

  1. temperaturethe mixture was warmed to room temperature over 5 hours
  2. extractionThen, the organic layer was extracted twice with 100 mL diethyl ether
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4d9d01d450f40cdaf3744a2ce9b8a3a
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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