2-Hydrazinoethanol → 8-(2-chlorophenylamino)-6,7-difluoro-2-(2-hydroxyethyl)-2H-phthalazin-1-one

HRID 1723692Notes

Reaction equation

HRID 1723692 reaction equation
CO[C:3](=[O:22])[C:4]1[C:9]([CH:10]=O)=[CH:8][C:7]([F:12])=[C:6]([F:13])[C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21].[OH:23][CH2:24][CH2:25][NH:26][NH2:27]>CCO>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:5]1[C:6]([F:13])=[C:7]([F:12])[CH:8]=[C:9]2[C:4]=1[C:3](=[O:22])[N:26]([CH2:25][CH2:24][OH:23])[N:27]=[CH:10]2

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 865985962-(2-Chlorophenylamino)-3,4-difluoro-6-formylbenzoic acid methyl ester

Product 1

HCID 674057088-(2-chlorophenylamino)-6,7-difluoro-2-(2-hydroxyethyl)-2H-phthalazin-1-oneYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-6-formyl benzoic acid methyl ester (0.400 mg, 1.228 mmol) and 2-hydroxyethyl hydrazine (0.102 mL, 1.351 mmol) in EtOH (10 mL) was heated at reflux under N2 for 16 hours. After cooling to room temperature, a yellow precipitate formed which was collected by filtration. The yellow solid was washed with EtOH and dried to yield 0.128 g (30%) pure desired product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 16 hours
  3. customa yellow precipitate formed which
  4. filtrationwas collected by filtration
  5. washThe yellow solid was washed with EtOH
  6. customdried

Sources & evidence

ORD record
ord-e95b2c5d6ba84b10b33aa812c3048444
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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