Formic Acid → N-formyl-2-amino-3',5-di-t-butyl biphenyl

HRID 924566Notes

Reaction equation

HRID 924566 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1.[CH:22](O)=[O:23]>O>[CH:22]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:9])([CH3:10])[CH3:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1)=[O:23]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 66813837HCID 66813837, compound

Product 1

HCID 86614227N-formyl-2-amino-3',5-di-t-butyl biphenylYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Added 2-amino-3′,5-di-t-butyl biphenyl (2.0 g, 7.11 mmol) to a solution of formic acid and heated to reflux for 16 hours. After cooling, water (25 mL) was added the product and the precipitate collected by vacuum filtration. The crude product was dissolved into ethyl acetate, washed with water. The organics were dried over magnesium sulfate and concentrated and purified by column chromatography using 10% ethyl acetate and hexanes as the eluants to give the pure N-formyl-2-amino-3′,5-di-t-butyl biphenyl (1.8 g, 82% yield) as determined by GCMS.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate collected by vacuum filtration
  5. dissolutionThe crude product was dissolved into ethyl acetate
  6. washwashed with water
  7. dry with materialThe organics were dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-76146ba73eac46539dbc939fe2f44d32
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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