4'-Chloro-3'-nitroacetophenone → HCID 89897925, compound

HRID 1410187Notes

Reaction equation

HRID 1410187 reaction equation
C([O-])(=O)C.[NH4+].[BH3-][C:7]#[N:8].[Na+].C[C:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=O.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH3:11])([CH2:7][NH2:8])[CH2:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 795964'-Chloro-3'-nitroacetophenoneHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 89897925HCID 89897925, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium acetate (3.86 g, 50 mmol), NaBH3CN (0.22 g, 3.5 mmol), and 3 Å molecular sieves (25 g) were added to a mixture of 4-chloro-3-nitroacetophenone (1.00 g, 5 mmol) in MeOH (15 mL) at rt. The mixture was stirred at rt for 20 h and NaHCO3 (aq, sat) and EtOAc were added. The mixture was filtered and the aq layer washed with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to give the sub-title compound. Yield: 0.27 g (27%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe aq layer washed with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-747f4fee522c4741be133729ad7ad82c
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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