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Sodium borohydride → (+/-)-6-[(4-chlorophenyl)hydroxymethyl]-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinone

HRID 1739829
Notes
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Reaction equation

HRID 1739829 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH3:29])[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:7])[C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH3:29])[CH:21]=2)=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 218374796-(4-chlorobenzoyl)-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinone

Product 1

HCID 21837484(+/-)-6-[(4-chlorophenyl)hydroxymethyl]-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinoneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of interm. (7-i) (3.55 g) in methanol (20 ml) and THF (20 ml) was cooled. Sodium borohydride (0.37 g) was added portionwise. The mixture was stirred at room temperature for 30 minutes, hydrolized and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 3.5 g (100%) of (±)-6-[(4-chlorophenyl)hydroxymethyl]-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinone (interm. 7-j).

Workup

  1. extractionhydrolized and extracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-518d7e08f5634b4fa1b3c339ea6c09e3
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05968952

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes