Pyridine → HCID 22905642, compound

HRID 1488465Notes

Reaction equation

HRID 1488465 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[C:18]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:10])=[C:4]([CH3:11])[CH:3]=1)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 41660974-Methoxy-3,5-dimethylaniline

Product 1

HCID 22905642HCID 22905642, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into an ice-cold solution of aniline 4 (15.1 g, 100 mmol) dissolved in methylene chloride (100 mL) were added sequentially pyridine (17.5 mL) and pivaloyl chloride (12.3 mL, 100 mmol) dropwise, and the resulting mixture was stirred at room temperature for 15 h. The mixture was diluted with methylene chloride and washed sequentially with 10% aq. hydrochloric acid, saturated aq. sodium bicarbonate and brine. Removal of solvents after drying (MgSO4) gave the pivalamide (19.8 g, 86% yield) as a pale brown solid, mp 126°-128° C. Spectral data: 1H NMR: δ 1.30 (s, 9H), 2.23 (s, 6H), 3.68 (s, 3H), 7.18 (s, 2H).

Workup

  1. washwashed sequentially with 10% aq. hydrochloric acid, saturated aq. sodium bicarbonate and brine
  2. customRemoval of solvents
  3. dry with materialafter drying (MgSO4)

Sources & evidence

ORD record
ord-1d11dd6e111e4854ba55706805921a00
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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