Hydrazine → HCID 68984729, compound

HRID 1822149Notes

Reaction equation

HRID 1822149 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH:7]=[C:8]1[CH:12]=[C:11]([CH2:13]C)[C:10](=O)[O:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][NH2:18].O.NN>CN1C(=O)CCC1.O>[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:12]=[C:11]([CH3:13])[C:10](=[O:9])[NH:18][N:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 68982264HCID 68982264, compound

Product 1

HCID 68984729HCID 68984729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
127.5 °C

Procedure

To a solution of lactone 18 (2.68 Kg; 12.77 mol) in 7.5 L of NMP cooled to below 0° C. was added 420 mL of anhydrous hydrazine (equivalent quantities of hydrazine hydrate also can be used) while maintaining the internal temperature at less than 20° C. After the addition was completed the reaction mixture was heated to 110-145° C. for one to five h. The reaction mixture was cooled and diluted with H2O (11 L) which resulted in the formation of crystalline pyridazinone 10 which was filtered and washed with water (2×2 L) and dried to afford 2.23 Kg (77.9%) of product.

Workup

  1. temperaturewhile maintaining the internal temperature at less than 20° C
  2. additionAfter the addition
  3. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-0a979636709f4804bfbe7fce489c7c64
Source dataset
uspto-grants-2009_10
Patent number
US07608731B2

Reaction notes

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