Hydrochloric Acid → 8-(2-chlorophenylamino)-6,7-difluoro-4-methyl-2H-phthalazin-1-one

HRID 1723688Notes

Reaction equation

HRID 1723688 reaction equation
[C:1]([C:4]1[C:9]([C:10](O)=[O:11])=[C:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:7]([F:21])=[C:6]([F:22])[CH:5]=1)(=O)[CH3:2].O.[NH2:24][NH2:25].Cl>C1COCC1.CCOC(C)=O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:8]1[C:7]([F:21])=[C:6]([F:22])[CH:5]=[C:4]2[C:9]=1[C:10](=[O:11])[NH:25][N:24]=[C:1]2[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 860527646-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

Product 1

HCID 674043668-(2-chlorophenylamino)-6,7-difluoro-4-methyl-2H-phthalazin-1-oneYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (62 mg, 0.19 mmol, prepared by the procedures described in Example 1) and hydrazine monohydrate (0.031 mL, 0.63 mmol) in THF (3 mL) was added catalytic amount of 1 N aqueous HCl (0.15 mL, 0.15 mmol) at room temperature. After stirring for 16 hours at room temperature, the reaction mixture was diluted with EtOAc, and washed with water (2×) and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the desired product (53 mg, 86%) that was used directly without further purification.

Workup

  1. washwashed with water (2×) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81c318642c2f4dcbbb858c7dec59d740
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

Loading…