Ethanol → HCID 14423301, compound

HRID 1197036Notes

Reaction equation

HRID 1197036 reaction equation
[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10](=[O:17])[C:9]3[CH2:18][C:19](=[O:22])[CH2:20][CH2:21][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)C>O>[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10](=[O:17])[C:9]3[CH2:18][CH:19]([OH:22])[CH2:20][CH2:21][C:8]2=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 14423300HCID 14423300, compound

Product 1

HCID 14423301HCID 14423301, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reduce 6,8,9,10-tetrahydro-10-phenylbenzo[b][1,8]naphthyridin-5,7-dione (2 mmol) with sodium borohydride (50 mg) in a solvent of ethanol (30 ml) and water (0.25 ml). After 15 minutes, pour the reaction mixture over ice and collect the resulting precipitate on a filter. Reserve the precipitate, and extract the aqueous filtrate with chloroform. Dry the extracts, evaporate the chloroform, and combine the residue with the reserved precipitate to give the product, 10-phenyl-7-hydroxy-6,7,8,9-tetrahydro-benzo[b][1,8]naphthyridin-5(10H)-one, m.p. 283°-286° C. after crystallization from ethanol.

Workup

  1. additionpour the reaction mixture over ice
  2. customcollect the resulting precipitate on a filter
  3. extractionReserve the precipitate, and extract the aqueous filtrate with chloroform
  4. customDry the extracts
  5. customevaporate the chloroform

Sources & evidence

ORD record
ord-806bc7b012a840108b17e9d06637b584
Source dataset
uspto-grants-1992_05
Patent number
US05116840

Reaction notes

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