Acetic Acid → HCID 59540398, compound

HRID 923441Notes

Reaction equation

HRID 923441 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 855054-Chloro-3-nitrobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59540398HCID 59540398, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzaldehyde (10.0 g, 53.9 mmol) and aniline (2.34 mL, 25.7 mmol) in ethanol (200 mL) was added acetic acid (7.35 mL, 128 mmol), followed by the portion-wise addition of sodium cyanoborohydride (4.84 g, 77 mmol). The resulting mixture was stirred at rt for 2.5 hrs and concentrated to vacuo. The residue was partitioned between ethyl acetate and saturated aq. NaHCO3, and the organic layer was dried over anhydrous Na2SO4. The drying agent was filtered off, and solvent was removed in vacuo to give a crude product that was purified by column chromatography on silica gel using a solvent gradient of 0-1% methanol in dichloromethane to give the title compound (5.7 g, 85%).

Workup

  1. concentrationconcentrated to vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated aq. NaHCO3
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationThe drying agent was filtered off
  5. customsolvent was removed in vacuo
  6. customto give a crude product that
  7. customwas purified by column chromatography on silica gel using a solvent gradient of 0-1% methanol in dichloromethane

Sources & evidence

ORD record
ord-4921d85f3ef34313b65e66ebb35631fd
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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