Water → HCID 178499523, compound

HRID 563987Notes

Reaction equation

HRID 563987 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH:13]([C:19](=O)[CH3:20])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=O)=[CH:7][CH:6]=1.O>C(O)C>[CH3:18][O:17][C:15](=[O:16])[CH2:14][C:13]1[C:19]([CH3:20])=[N:2][NH:3][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([Cl:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 67004944Methyl 3-[(4-chlorophenyl)carbonyl]-4-oxopentanoate

Product 1

HCID 178499523HCID 178499523, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.236 g (45 mmol) of hydrazine hydrate were added to a solution of 10 g (37 mmol) of methyl 3-[(4-chlorophenyl)carbonyl]-4-oxopentanoate in ethanol (100 ml). The mixture was heated under reflux for 6 hours and then added to water and extracted with dichloromethane. The combined organic phases were dried with magnesium sulfate, filtered and concentrated. This gave 6.9 g of product (63% of theory); NMR (CDCl3, 400 MHz): 2.28 (s, 3H); 3.5 (s, 2H); 3.7 (s, 3H); 7.39 (d, 2H); 7.5 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11eb647f8a584551ad8f923147522b70
Source dataset
uspto-grants-2011_11
Patent number
US08067611B2

Reaction notes

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