Acetic Acid → HCID 55832913, compound

HRID 602511Notes

Reaction equation

HRID 602511 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[NH2:17].C([BH3-])#N.[Na+].C(O)(=O)C>CC1C=CC=CC=1C.C(OCC)(=O)C>[CH3:13][C:14]1[CH:15]=[C:16]([NH:17][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 118984-Nitro-m-toluidineHCID 679964-(Trifluoromethyl)benzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 55832913HCID 55832913, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 4-trifluoromethylbenzaldehyde (819 μL, 6.00 mmol), 3-methyl-4-nitroaniline (609 mg, 4.00 mmol), and Amberlite IRC-84 (200 mg, H+ form) in o-xylene (4 mL) was heated under nitrogen at 140° C. for 6 hours. It was then cooled to room temperature, diluted with ethyl acetate (5 mL), dried over sodium sulfate, filtered, and volatiles were evaporated. The residue was dissolved in acetonitrile (20 mL) and sodium cyanoborohydride (503 mg, 8.00 mmol) was added in one portion, followed by acetic acid (1 mL) in several portions over 15 minutes. After a further 30 minutes solvents were evaporated and the residue was partitioned between ethyl acetate (50 mL), brine (25 mL), and 10% aqueous potassium carbonate (25 mL). The organic layer was dried over sodium sulfate, solvents were evaporated, and the residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures) to yield the title compound as a yellow powder (1.02 g, 82%).

Workup

  1. temperatureIt was then cooled to room temperature
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customvolatiles were evaporated
  5. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  6. customAfter a further 30 minutes solvents were evaporated
  7. customthe residue was partitioned between ethyl acetate (50 mL), brine (25 mL), and 10% aqueous potassium carbonate (25 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate, solvents
  9. customwere evaporated
  10. customthe residue was purified on a FlashMaster system (silica, eluted with heptane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-88c530bc50a34b66a59a2cb25d40f882
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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