Water → 4-(4-Acetylaminophenyl)-1,2-Dihydro-6-Methylthiophthalazine

HRID 2181611Notes

Reaction equation

HRID 2181611 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH:14]=[N:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[BH3-]C#N.[Na+].O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:21][CH3:22])[CH:19]=3)[CH2:14][NH:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 99444901-(4-Acetylaminophenyl)-7-Methylthiophthalazine

Product 1

HCID 129861744-(4-Acetylaminophenyl)-1,2-Dihydro-6-MethylthiophthalazineYield 74.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the phthalazine 7 (130 mg, 0.42 mmol) in acetic acid (7 mL) was added NaBH3CN in portions. After stirring for 15 min, water was added. The aqueous phase was neutralized by NaHCO3, and then extracted with DCM. The combined organic phase was dried over Na2SO4. Removal of the solvent afforded the product (97 mg, 74%) which can be used directly for next step.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-c89595f156fd49b1b5824748a7f5734c
Source dataset
uspto-grants-2005_05
Patent number
US06894048B2

Reaction notes

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