Sodium Hydroxide → HCID 66965572, compound

HRID 2036844Notes

Reaction equation

HRID 2036844 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]#[N:15].[OH-:16].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]([NH2:15])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 463118033-Amino-biphenyl-2-carbonitrile

Product 1

HCID 66965572HCID 66965572, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-aminobiphenyl-2-carbonitrile (4 g, 20 mmol) in ethanol (20 mL) and aqueous NaOH (8 g, 200 mmol) was heated at 100° C. in the microwave reactor for 1 h 30 min. After this time, the ethanol was evaporated under reduced pressure and the resulting residue was extracted with ethyl acetate. The organic extracts were concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography (50% EtOAc in hexane) to give 3-aminobiphenyl-2-carboxamide (3.1 g, 72% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.40-7.30 (m, 5H), 7.15 (br s, 1H), 7.11 (t, 1H, J=8 Hz), 6.72 (dd, 1H, J=0.8, 8 Hz), 6.52 (dd, 1H, J=0.8, 8 Hz), 5.13 (s, 1H). LCMS Method W: retention time 1.28 min; [M+1]=213.0.

Workup

  1. customAfter this time, the ethanol was evaporated under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. concentrationThe organic extracts were concentrated under reduced pressure
  4. customto yield a residue
  5. customThe residue was purified by silica gel chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-6401f6a4089447fc8fb377e48bd94216
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

Loading…