Ammonium Chloride → HCID 45095638, compound

HRID 916695Notes

Reaction equation

HRID 916695 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]1[C:9]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:8][C:7]([CH:18]=[O:19])=[N:6]1)[CH3:4].[NH4+].[Cl-]>CCO>[CH2:3]([N:5]1[C:9]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:8][C:7]([CH2:18][OH:19])=[N:6]1)[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 45095564HCID 45095564, compound

Product 1

HCID 45095638HCID 45095638, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (252 mg, 6.6 mmol) was added portionwise to a stirred solution of 3-(1-ethyl-3-formyl-1H-pyrazol-5-yl)-benzonitrile (1.5 g, 6.6 mmol) in EtOH (25 mL) at 0° C. The mixture was warmed to RT and stirred for a further 30 min., NH4Cl solution (10 ml) was added, the EtOH removed under reduced pressure, H2O (30 mL) added, and the aqueous mixture extracted with EtOAc (2×70 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4) and concentrated under reduced pressure to yield the crude alcohol (1.49 g, quant.). 1H NMR (CDCl3, 360 MHz) δ 7.78-7.54 (4H, m), 6.31 (1H, s), 4.72 (2H, s), 4.11 (2H, q, J=7.3 Hz), 1.42 (3H, t, J=7.3 Hz). MS (ES+) C13H13N3O requires: 227, found: 228 (M+H+, 70%).

Workup

  1. customthe EtOH removed under reduced pressure, H2O (30 mL)
  2. additionadded
  3. extractionthe aqueous mixture extracted with EtOAc (2×70 mL)
  4. washThe combined organic extracts were washed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91c576729940482485de9edec23803cb
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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