Pyridine → HCID 22347586, compound

HRID 1419948Notes

Reaction equation

HRID 1419948 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[CH:17]=[CH:18][C:19](Cl)=[O:20]>ClCCl>[CH3:11][O:10][N:9]([CH3:8])[C:19](=[O:20])/[CH:18]=[CH:17]/[C:16]1[CH:22]=[CH:23][CH:24]=[C:14]([O:13][CH3:12])[CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 543303913-Methoxycinnamoyl Chloride

Product 1

HCID 22347586HCID 22347586, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methoxycinnamic acid (75.0 g, 0.42 mol) in thionyl chloride (250 mL) was heated at reflux for 1 h. The majority of the the thionyl chloride was then distilled off and the resulting residue was treated with dichloromethane and residual thionyl chloride was removed by codistillation to give 3-methoxycinnamic acid chloride of sufficient purity to be used without further purification. Pyridine (186 mL, 2.3 mol) and N,O-dimethylhydroxylamine hydrochloride (45.17 g, 0.46 mol) were added to a 0° C. solution of 3-methoxycinnamic acid chloride(0.42 mol) in dry dichloromethane (500 mL). The solution was stirred for 18 h at room temperature, diluted with dichloromethane (200 mL), and washed sequentially with 1N HCl, saturated sodium bicarbonate, and brine. It was then dried over MgSO4 and concentrated in vacuo to give the title compound as a dark oil (88.43 g, 95%): 1H NMR (300 MHz, CDCl3) δ 3.25 (s, 3H), 3.68 (s, 3H), 3.84 (s, 3H), 6.82-6.86 (m, 1H), 7.00 (d, J=16.1 Hz, 1H), 7.10 (br s, 1H), 7.15-7.20 (m, 1H), 7.32 (t, J=6.6 Hz, 1H), 7.72 (d, J=16.0 Hz, 1H).

Workup

  1. customto be used without further purification
  2. washwashed sequentially with 1N HCl, saturated sodium bicarbonate, and brine
  3. dry with materialIt was then dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd6a4f398b2048739c0fbf487bbe2a89
Source dataset
uspto-grants-1999_03
Patent number
US05889031

Reaction notes

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