2-Chloroaniline → ethyl 4-(4-chlorophenyl)-2-[(2-chlorophenyl)hydrazinylidene]-3-oxobutanoate

HRID 859182Notes

Reaction equation

HRID 859182 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].[CH2:13]([O:15][C:16](=[O:28])[CH2:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH3:14]>O.C(O)(=O)C>[CH2:13]([O:15][C:16](=[O:28])[C:17](=[N:1][NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[Cl:5])[C:18](=[O:27])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH3:14]

Participants

6

Reactant 3

HCID 72402-ChloroanilineHCID 10847663Ethyl 4-(4-chlorophenyl)-3-oxobutanoateHCID 23668193Sodium Nitrite

Product 1

HCID 178472847ethyl 4-(4-chlorophenyl)-2-[(2-chlorophenyl)hydrazinylidene]-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (3.4 g, 50.4 mmol) in water (15 ml) was added dropwise over an hour period to a cooled (0° C.), stirred solution of 2-chloroaniline (6.4 g, 50.4 mmol) in acetic acid (50 ml)/water (7 ml). Then a solution of 4-(4-chloro-phenyl)-3-oxo-butyric acid ethyl ester (10 g, 42 mmol) in acetic acid (30 ml) was added dropwise over a 30-minutes period to produce an orange slurry (20 ml of water added to aid stirring). After an additional hour, the mixture was filtered, solids washed with water and air-dried. Solids slurried in ethanol (75 ml) for 30 minutes, filtered, solids washed with methanol and dried in vacuo to afford the title compound (I-2b) as an orange solid, 11.0 g.

Workup

  1. customto produce
  2. waitAfter an additional hour
  3. filtrationthe mixture was filtered
  4. washsolids washed with water
  5. customair-dried
  6. filtrationfiltered
  7. washsolids washed with methanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6915ab0a748b40a886b36700fd97ff80
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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