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

HRID 2363776Notes

Reaction equation

HRID 2363776 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-fb7b4db3ad414e50be7dfa13b4c8324d
Source dataset
uspto-grants-2014_04
Patent number
US08691988B2

Reaction notes

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