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Sodium borohydride → 7-(Hydroxymethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422527
Notes
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Reaction equation

HRID 2422527 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:1][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 574378457-Formyl-4-phenylquinoline-2-carbonitrile

Product 1

HCID 597748927-(Hydroxymethyl)-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-formyl-4-phenylquinoline-2-carbonitrile (516 mg, 2.0 mmol) in THF (6 mL) and MeOH (2 mL) was added at 0° C. sodium borohydride (91 mg, 2.4 mmol). The mixture was stirred 1 h at 0° C., quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The compound was used as such for the next step. MS (+ESI): 262 (M+H)+.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69420fec5eff41828e4cd9114ab39e77
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960409B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes