Hydrochloric Acid → HCID 9927383, compound

HRID 1616739Notes

Reaction equation

HRID 1616739 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O.C([CH2:22][C:23]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)=[O:24])(O)=O.Cl>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:22]/[C:23]([NH:25][C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)=[O:24])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 8419VeratraldehydeHCID 4387480HCID 4387480, compound

Product 1

HCID 9927383HCID 9927383, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.39 mL, 4.0 mmol) was added to a suspension of 3,4-dimethoxybenzaldehyde (0.66 g, 4.0 mmol) and 4-[(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. The crude product was recrystallised from EtOH providing (E)-4-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.58 g, 53%) as a yellow crystalline solid; mp 258-259° C., lit. [24] 267-269° C.; δH (400 MHz, DMSO-d6) 3.80 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 6.72 (d, J=15.6 Hz, 1H, CH═CHCO), 7.01 (d, J5′,6′=8.2 Hz, 1H, H5′), 7.20 (d, J5′,6′=8.2 Hz, 1H, H6′), 7.22 (s, 1H, H2′), 7.56 (d, J=15.6 Hz, 1H, CH═CHCO), 7.80 (d, J2,3=J5,6=8.4 Hz, 2H, H3, H5), 7.90 (d, J2,3=J5,6=8.4 Hz, 1H, H2, H6), 10.43 (s, 1H, NH), 12.68 (br s, 1H, CO2H).

Workup

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

Sources & evidence

ORD record
ord-7070e63c3e5f459bba3944389310a35e
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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