Ammonia → HCID 19079121, compound

HRID 6177Notes

Reaction equation

HRID 6177 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[N:3]1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[BH4-].[Na+].O.N>FC(F)(F)C(O)=O>[C:2]1(=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4311764Sodium borohydrideHCID 190791664-(3-Hydroxyisoindolin-1-on-2-ylmethylthio)pyridine

Product 1

HCID 19079121HCID 19079121, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 681 mg (2.5 mmol) of 4-[(3-hydroxyisoindolin-1-on-2-yl)methylthio]pyridine in 6 ml of trifluoroacetic acid, 0.30 g (7.93 mmol) of sodium borohydride was added in small portions, and the mixture was stirred for 15 minutes. The reaction mixture was poured into cold water and aqueous ammonia was added to make the mixture basic, followed by extraction with methylene chloride. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by recrystallization (solvent: ethyl acetate) to give 350 mg of the desired product (54.6% yield, colorless columns), mp. 131°-132° C.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by recrystallization (solvent: ethyl acetate)

Sources & evidence

ORD record
ord-bcf7a1386a3647debe56a5b796b263a1
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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