Acetic Acid → HCID 24855507, compound

HRID 1616789Notes

Reaction equation

HRID 1616789 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.C([CH2:20][C:21]([NH:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=[O:27])=[O:22])(O)=O.CC(O)=O>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:20]/[C:21]([NH:23][C:24]2[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=2[C:26]([OH:28])=[O:27])=[O:22])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 24855507HCID 24855507, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (220 μL, 2.2 mmol) was added to a suspension of 6-methoxy-3-pyridine carboxaldehyde (0.30 g, 2.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.44 g, 2.1 mmol) in toluene (5 mL) and treated according to Procedure 2, acidifying with 20% AcOH. The crude product was recrystallised from EtOH providing (E)-2-[[3-(6-methoxypyridin-3-yl)-1-oxo-2-propenyl]amino]benzoic acid (0.33 g, 56%) as a colourless crystalline solid; mp 209-211° C.; δH (400 MHz, DMSO-d6) 3.85 (s, 3H, OCH3), 6.82 (d, J=15.6 Hz, 1H, CH═CHCO), 6.85 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.13 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.57 (d, J=15.6 Hz, 1H, CH═CHCO), 7.58 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 7.98 (d, J3,4=8.0 Hz, 1H, H3), 8.14 (dd, J5′,6′=8.0, J2′6′=1.6 Hz, 1H, H6′), 8.43 (d, J2′,6′=1.6 Hz, 1H, H2′), 8.57 (d, J5,6=8.0 Hz, 1H, H6), 11.29 (s, 1H, NH), 13.58 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 53.5, 111.0, 116.7, 120.3, 121.4, 122.8, 124.2, 131.1, 134.0, 137.3, 138.0, 140.9, 148.4, 163.7, 164.4, 169.4; HRMS (ESI) calculated for C16H14N2O4 [M−H]− 297.0870. found 297.0877; vmax 749, 1249, 1591, 1683, 3246 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was recrystallised from EtOH

Sources & evidence

ORD record
ord-7ba2df0e7d264d5aa9ee52ba53cc9dc9
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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