Pyridine → HCID 10872834, compound

HRID 1785408Notes

Reaction equation

HRID 1785408 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH:12]=[C:13]2[C:18]3=[N:19][C:20]4[C:21]([CH3:27])=[CH:22][CH:23]=[CH:24][C:25]=4[CH:26]=[C:17]3[C:16](=[O:28])[O:15][C:14]2=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].NC1C=C(OC)C(OC)=CC=1.N1C=CC=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH:12]=[C:13]([C:14]([OH:15])=[O:29])[C:18]3[N:19]=[C:20]4[C:21]([CH3:27])=[CH:22][CH:23]=[CH:24][C:25]4=[CH:26][C:17]=3[C:16]2=[O:28])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 227703,4-DimethoxyanilineHCID 178492245HCID 178492245, compound

Product 1

HCID 10872834HCID 10872834, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 19 (0.23 g), 4-aminoveratrole (0.46 g), pyridine (15 mL) and triethylamine (1 mL) was heated under reflux for 8 h (dissolution occurred during the heating). The reaction mixture was allowed to stand at −10° C. overnight and the resulting precipitate was collected by filtration and washed with a little cold acetone to give the product as a yellow solid (0.18 g, 78%), mp 297-298° C. (after forming needles->285° C.). 1H NMR (d6-DMSO): δ 2.73 (s, 3H, CH3), 3.78 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 7.12 (s, 2H), 7.23 (s, 1H), 7.67 (t, 1H, J=7.4 Hz, H-8), 7.95 (d, 1H, J=6.7 Hz), 8.23 (d, 1H, J=8.2 Hz), 8.45 (s, 1H), 9.50 (s, 1H, H-10), 15.98 (br s, 1H, COOH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h (
  3. dissolutiondissolution
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with a little cold acetone
  6. customto give

Sources & evidence

ORD record
ord-b9f74c0ecd3c4190be12e42e72312709
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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