Sodium borohydride → HCID 14373257, compound

HRID 414554Notes

Reaction equation

HRID 414554 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[C:2]1([CH:1]([OH:8])[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14373255120067-47-2

Product 1

HCID 14373257HCID 14373257, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 3.0 g of 6-benzoyl-3,4-dihydrocarbostyril in 120 ml of methanol was treated at 0° C. with 1.2 g of sodium borohydride. The mixture was stirred at 25° C. for 18 hours during which time the suspended solid dissolved. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol in methylene chloride and water. The extract was dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to give 6-(phenylhydroxymethyl)-3,4-dihydrocarbostyril, m.p. 166°-169° C.

Workup

  1. dissolutiondissolved
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between 10% methanol in methylene chloride and water
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b297192cf63f4745896ba507928ef611
Source dataset
uspto-grants-1988_12
Patent number
US04792561

Reaction notes

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