Sodium borohydride → 2-(Hydroxymethyl)-6-nitrobenzonitrile

HRID 471674Notes

Reaction equation

HRID 471674 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:6]=1[C:7]#[N:8])=[O:4]>CO.C1COCC1>[OH:4][CH2:3][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:6]=1[C:7]#[N:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866574742-Formyl-6-nitrobenzonitrile

Product 1

HCID 674010342-(Hydroxymethyl)-6-nitrobenzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (92.0 mg, 2.43 mmol) was added to a solution of 2-formyl-6-nitrobenzonitrile (Example 207e) (0.86 g, 4.88 mmol) in MeOH (38 mL) and THF (38 mL) at −8° C., and was stirred at that temperature for no more than 30 min. The reaction was quenched with HCl (6 M, 4.88 mL), followed by addition of water (50 mL), and brine (50 mL). The mixture was extracted with EtOAc, the combined extract was dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography on silica using the solvent gradient CH2Cl2→CH2Cl2/MeOH (8:2) to give the title compound in amount of 0.32 g, (37%), which was used immediately in the next step. 1H NMR (400 MHz, DMSO-d6) δ 4.77 (d, J=5.6 Hz, 2H), 5.87 (t, J=5.6 Hz, 1H), 7.97 (t, J=8.0 Hz, 1H), 8.07 (dd, J=0.4, 8.0 Hz, 1H), 8.28 (dd, J=0.8, 8.0 Hz, 1H).

Workup

  1. customThe reaction was quenched with HCl (6 M, 4.88 mL)
  2. additionfollowed by addition of water (50 mL), and brine (50 mL)
  3. extractionThe mixture was extracted with EtOAc
  4. extractionthe combined extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica using the solvent gradient CH2Cl2

Sources & evidence

ORD record
ord-203ae7d8d7334a2db128654b49e37864
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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