Hydrochloric Acid → 2-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic acid

HRID 1616729Notes

Reaction equation

HRID 1616729 reaction equation
N1CCCCC1.[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=O.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>[OH:7][C:8]1[CH:9]=[C:10](/[CH:11]=[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:13]=[CH:14][C:15]=1[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 87683,4-DihydroxybenzaldehydeHCID 4399222-(2-Carboxyacetamido)benzoic acid

Product 1

HCID 98610882-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.39 mL, 4.0 mmol) was added to a suspension of 3,4-dihydroxybenzaldehyde (0.55 g, 4.0 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.74 g, 3.3 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. (E)-2-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.82 g, 83%) was obtained as a brown crystalline solid; mp 204-206° C.; lit. [24] 204-206° C.; δH (500 MHz, DMSO-d6) 6.50 (d, J=15.5 Hz, 1H, CH═CHCO), 6.77 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.00 (dd, J5′,6′=8.0, =2.0 Hz, 1H, H6′), 7.08 (d, J2′,6′=2.0 Hz, 1H, H2′), 7.14 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.44 (d, J=15.5 Hz, 1H, CH═CHCO), 7.61 (td, J4,5=J5,6=8.0, J3,5=1.5 Hz, 1H, H5), 8.00 (dd, J3,4=8.0, J3,5=1.5 Hz, 1H, H3), 8.58 (d, J5,6=8.0 Hz, 1H, H6), 9.11 (s, 1H, OH), 9.52 (s, 1H, OH), 11.25 (s, 1H, NH).

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-c5febd456c584cc1b567e0f9b3e58ef0
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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