Pyridine → N-(4-methoxybiphenyl-2-yl)-2,2-dimethylpropionamide

HRID 617407Notes

Reaction equation

HRID 617407 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH2:15])[CH:4]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:15][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 27603632-Amino-4-methoxy-biphenyl

Product 1

HCID 21852181N-(4-methoxybiphenyl-2-yl)-2,2-dimethylpropionamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A magnetically stirred solution of 4-methoxybiphenyl-2-ylamine (25.27 g, 127 mmol) in CH2Cl2 (300 mL)/pyridine (300 mL) at 0° C. under nitrogen was treated with pivaloyl chloride via syringe (16.8 g, 17.2 mL, 139 mmol). The resultant suspension was stirred for 12 h at room temperature and concentrated in vacuo. The residue was digested with CH2Cl2 (300 mL), washed with 1 N HCl (2×300 mL), 1 N NaOH (2×300 mL), H2O (300 mL), brine (300 mL), dried (K2CO3), filtered, and concentrated in vacuo to give 33.6 g (93%) of a white solid: 1H NMR (300 MHz, CDCl3) δ 1.07 (s, 9H), 3.83 (s, 3H), 6.69 (dd, J=8.5, 2 Hz, 1H), 7.12 (d, J=8.5 Hz, 1H), 7.29-7.47 (m, 5H), 7.53 (br s, 1H), 8.13 (d, J=2 Hz, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with 1 N HCl (2×300 mL), 1 N NaOH (2×300 mL), H2O (300 mL), brine (300 mL)
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d67ddba6d9894f13978198d4e537c733
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

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