Hydrochloric Acid → 4-Methyl-3-(1-(2-methyl-4-(trifluoromethylsulfonyl)phenyl)phthalazin-6-yl)benzoic acid

HRID 422574Notes

Reaction equation

HRID 422574 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])=[CH:24][C:23]=1[CH3:35])=[N:17][N:16]=[CH:15]2.[OH-].[Na+].Cl>C1COCC1.CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([C:31]([F:33])([F:32])[F:34])(=[O:30])=[O:29])=[CH:24][C:23]=1[CH3:35])=[N:17][N:16]=[CH:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66674278Methyl 4-methyl-3-(1-(2-methyl-4-(trifluoromethylsulfonyl)phenyl)phthalazin-6-yl)benzoate

Product 1

HCID 666751944-Methyl-3-(1-(2-methyl-4-(trifluoromethylsulfonyl)phenyl)phthalazin-6-yl)benzoic acidYield 70.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 4-methyl-3-(1-(2-methyl-4-(trifluoromethylsulfonyl)phenyl)phthalazin-6-yl)benzoate (120 mg, 0.24 mmol) in 3 mL of 2/1 THF/MeOH was added NaOH (30 mg, 0.72 mmol) at RT. After 8 h, the mixture was acidified with 2M HCl and extracted with DCM (3×). The combined DCM layers were washed with brine, dried and concentrated to afford the 4-methyl-3-(1-(2-methyl-4-(trifluoromethylsulfonyl)phenyl)phthalazin-6-yl)benzoic acid (82 mg) as a tan solid. The crude acid was used in the next step. MS (ESI, pos. ion) m/z: 486.9 (M+1).

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined DCM layers were washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5df8d5d6ac2e40c98c8411427fd878f3
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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