Hydrochloric Acid → 2-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]amino}benzoic acid

HRID 1616728Notes

Reaction equation

HRID 1616728 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=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.Cl>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[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 313Hydrochloric AcidHCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 4399222-(2-Carboxyacetamido)benzoic acid

Product 1

HCID 24004272-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]amino}benzoic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.42 mL, 4.2 mmol) was added to a suspension of 4-methoxybenzaldehyde (0.51 mL, 4.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.83 g, 3.7 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. (E)-2-[[3-(4-Methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.95 g, 86%) was obtained as a pale yellow crystalline solid; mp 194-195° C., lit. [24] 195-198° C.; δH (500 MHz, DMSO-d6) 3.80 (s, 3H, OCH3), 6.72 (d, J=15.5 Hz, 1H, CH═CHCO), 6.98 (d, J2′,3′=J5′,6′=9.0 Hz, 2H, H3′, H5′), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.57 (d, J=15.5 Hz, 1H, CH═CHCO), 7.60 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 7.68 (d, J2′,3′=J5′,6′=9.0 Hz, 2H, H2′, H6′), 7.99 (d, J3,4=8.0 Hz, 1H, H3), 8.60 (d, J5,6=8.0 Hz, 1H, H6), 11.28 (s, 1H, NH).

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-e2d5ceae10154ba3a1389e2bd67a41c4
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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